1,126 results on '"*SULFONYL compounds"'
Search Results
2. Recent Advances in Developing Radical Methods for the Synthesis of Aliphatic Sulfonyl Fluorides.
- Author
-
Lin, Lu, Pei, Guanhua, Cao, Zhong‐Yan, and Liao, Saihu
- Subjects
- *
RADICALS (Chemistry) , *DRUG discovery , *CHEMICAL biology , *ORGANIC synthesis , *MATERIALS science , *SULFONYL compounds , *FLUORIDES - Abstract
Sulfonyl fluorides have widespread applications in many fields, including organic synthesis, chemical biology, drug discovery and materials science. In particular, in the past decade, a number of aliphatic sulfonyl fluorides have been identified showing various biological activities. These applications and appealing features of sulfonyl fluorides have brought about a significant advancement in developing synthetic methods to access sulfonyl fluorides. In this review, we will discuss the recent developments of radical approaches for the synthesis of aliphatic sulfonyl fluorides. [ABSTRACT FROM AUTHOR]
- Published
- 2024
- Full Text
- View/download PDF
3. Iodophor-Catalyzed Disulfenylation of Amino Naphthalenes with Aryl Sulfonyl Hydrazines.
- Author
-
Yuan, Yutong, He, Jing, Ma, Xiaowei, Han, Sheng, and Liu, Yan
- Subjects
- *
HYDRAZINES , *NAPHTHALENE , *BIOCHEMICAL substrates , *SULFIDES , *SULFUR , *HYDRAZINE , *SULFONYL compounds - Abstract
An iodophor-catalyzed direct disulfenylation of amino naphthalenes with aryl sulfonyl hydrazines in water was developed. A series of aryl sulfides were obtained in moderate to excellent yields. The advantages of this green protocol were the simple reaction conditions (metal-free, water as the solvent, under air), the odorless and easily available sulfur reagent, the broad substrate scope, and gram-scale synthesis. Moreover, the potential application of aryl sulfides was exemplified by further transformations. [ABSTRACT FROM AUTHOR]
- Published
- 2024
- Full Text
- View/download PDF
4. Synthesis of 5-oxo-1-[4-(aminosulfonyl)phenyl]pyrrolidine-3-carboxylic acids.
- Author
-
Serkov, S. A., Sigay, N. V., Kostikova, N. N., Tyurin, A. P., Kolotyrkina, N. G., and Gazieva, G. A.
- Subjects
- *
ITACONIC acid , *CHEMICAL synthesis , *ANTI-infective agents , *CONDENSATION , *SULFONYL compounds - Abstract
A series of new 1-[4-(aminosulfonyl)phenyl]-5-oxopyrrolidine-3-carboxylic acids were synthesized by the solvent-free condensation of 4-aminobenzenesulfonamides with itaconic acid at 140–165 °C. The synthesized compounds were examined for antimicrobial activity. [ABSTRACT FROM AUTHOR]
- Published
- 2024
- Full Text
- View/download PDF
5. Photoredox‐Catalyzed Preparation of Sulfones Using Bis‐Piperidine Sulfur Dioxide – An Underutilized Reagent for SO2 Transfer.
- Author
-
Griffiths, Oliver M., Esteves, Henrique A., Emmet, Darcy C., and Ley, Steven V.
- Subjects
- *
SULFUR dioxide , *SULFONYL compounds , *ALKYL bromides , *ARYL bromides , *SULFONYL group , *SULFONES - Abstract
Sulfonyl groups are widely observed in biologically relevant molecules and consequently, SO2 capture is an increasingly attractive method to prepare these sulfonyl‐containing compounds given the range of SO2‐surrogates now available as alternatives to using the neat gas. This, along with the advent of photoredox catalysis, has enabled mild radical capture of SO2 to emerge as an effective route to sulfonyl compounds. Here we report a photoredox‐catalyzed cross‐electrophile sulfonylation of aryl and alkyl bromides making use of a previously under‐used amine‐SO2 surrogate; bis(piperidine) sulfur dioxide (PIPSO). A broad selection of alkyl and aryl bromides were photocatalytically converted to their corresponding sulfinates and then trapped with various electrophiles in a one‐pot multistep procedure to prepare sulfones and sulfonamides. [ABSTRACT FROM AUTHOR]
- Published
- 2024
- Full Text
- View/download PDF
6. Novel Pitolisant-Derived Sulfonyl Compounds for Alzheimer Disease.
- Author
-
Pérez-Silanes, Silvia, Martisova, Eva, Moreno, Esther, Solas, Maite, Plano, Daniel, Sanmartin, Carmen, and Ramírez, María Javier
- Subjects
- *
SULFONYL compounds , *ALZHEIMER'S disease , *SCOPOLAMINE , *TROPANES , *PHARMACEUTICAL chemistry , *NEURODEGENERATION , *MEMORY loss - Abstract
Alzheimer's disease (AD) is a complex and multifactorial neurodegenerative disorder characterized by cognitive decline, memory loss, behavioral changes, and other neurological symptoms. Considering the urgent need for new AD therapeutics, in the present study we designed, synthesized, and evaluated multitarget compounds structurally inspired by sulfonylureas and pitolisant with the aim of obtaining multitarget ligands for AD treatment. Due to the diversity of chemical scaffolds, a novel strategy has been adopted by merging into one structure moieties displaying H3R antagonism and acetylcholinesterase inhibition. Eight compounds, selected by their binding activity on H3R, showed a moderate ability to inhibit acetylcholinesterase activity in vitro, and two of the compounds (derivatives 2 and 7) were also capable of increasing acetylcholine release in vitro. Among the tested compounds, derivative 2 was identified and selected for further in vivo studies. Compound 2 was able to reverse scopolamine-induced cognitive deficits with results comparable to those of galantamine, a drug used in clinics for treating AD. In addition to its efficacy, this compound showed moderate BBB permeation in vitro. Altogether, these results point out that the fragment-like character of compound 2 leads to an optimal starting point for a plausible medicinal chemistry approach for this novel strategy. [ABSTRACT FROM AUTHOR]
- Published
- 2024
- Full Text
- View/download PDF
7. Cobalt(II) catalytic oxidation of arylmethyl sulfonyl imines to arylcarbonyl analogues.
- Author
-
Zetao Ma, Peipei Ma, Hongli Wu, and Haifeng Gan
- Subjects
- *
CATALYTIC oxidation , *IMINES , *COBALT , *ISOTHIAZOLE , *SULFONYL compounds - Abstract
A novel Co(OAc)2/N-hydroxyphthalimide (NHPI)-catalyzed oxidation of 3-arylmethyl sulfonyl imines to prepare 3-arylcarbonyl analogues has been realized. 3-Arylcarbonyl sulfonyl imines were comprehensively synthesized from benzyl substrates for the first time. The reactions proceeded in moderate to excellent yields. Mechanistic investigation suggests that 3-(hydroperoxy(phenyl)methyl)benzo[d]isothiazole 1,1-dioxide A is the key intermediate for the formation of products 2. [ABSTRACT FROM AUTHOR]
- Published
- 2024
- Full Text
- View/download PDF
8. One‐Pot Access to 3‐Sulfonyl Flavones via K2CO3‐Mediated Annulation of α‐Sulfonyl o‐Hydroxyacetophenones with Substituted Nitriles.
- Author
-
Chang, Meng‐Yang and Lin, Chun‐Yi
- Subjects
- *
NITRILES , *DOUBLE bonds , *SCISSION (Chemistry) , *ANNULATION , *FLAVONES , *SULFONYL compounds - Abstract
The one‐pot construction of diversified sulfonyl flavones was developed by K2CO3‐mediated formal (5+1) stepwise annulation of α‐sulfonyl o‐hydroxyacetophenones with substituted nitriles under the open‐flask atmosphere conditions. A plausible mechanism is proposed and discussed. This method provides intermolecular and intramolecular ring‐closure via the formations of one carbon‐oxygen single (C−O) bond, one carbon‐carbon (C=C) double bond, and the cleavage of one carbon‐nitrile triple (C≡N) bond. [ABSTRACT FROM AUTHOR]
- Published
- 2023
- Full Text
- View/download PDF
9. One‐Pot Synthesis of Bis‐sulfonyl Dibenzofurans via K2CO3‐Mediated Benzannulation of α‐Sulfonyl o‐Hydroxyacetophenones with 1,4‐Dichloro‐2‐butyne.
- Author
-
Chang, Meng‐Yang, Lee, Yan‐Ling, and Chen, Hsing‐Yin
- Subjects
- *
DIBENZOFURANS , *DOUBLE bonds , *POLYCHLORINATED dibenzodioxins , *SULFONYL compounds - Abstract
A one‐pot synthesis method for functionalized bis‐sulfonyl dibenzofurans was developed under an air atmosphere using potassium carbonate‐mediated benzannulation of diversified α‐sulfonyl o‐hydroxyacetophenones with 1,4‐dichloro‐2‐butyne. A plausible mechanism was proposed and discussed. This method provides intermolecular double α‐propargylation, sulfonyl migration, and intramolecular ring‐closure via the formation of one carbon‐oxygen single (C−O) bond, one carbon‐sulfur single (C−S) bond, and two carbon‐carbon (C=C) double bonds. [ABSTRACT FROM AUTHOR]
- Published
- 2023
- Full Text
- View/download PDF
10. Synthesis of Indole-1,3,4-oxadiazole Based Sulfonyl 1,2,4-Oxadiazole Derivatives as EGFR Targeting Anticancer Agents.
- Author
-
Dubba, Abhilasha and Koppula, Shiva Kumar
- Subjects
- *
EPIDERMAL growth factor receptors , *ANTINEOPLASTIC agents , *PROTEIN-tyrosine kinases , *BENZOIC acid , *THIADIAZOLES , *SULFONYL compounds , *CYTOTOXINS - Abstract
A series of indole-based 1,3,4-oxadiazole-linked sulfonyl 1,2,4-oxadiazole derivatives were synthesized using 2-{[5-(1H-indol-2-yl)-1,3,4-oxadiazol-2-yl]sulfonyl}acetonitrile and widely available substituted benzoic acid in pursuit of better anticancer drugs. The novel synthesized compounds were tested for cytotoxicity against MCF-7 and A-549 in vitro. Six of the screened compounds were shown to be active against the tested cell lines. The most active compounds were further tested for their efficacy in inhibiting the tyrosine kinase EGFR, and the results showed that compounds 3-({[5-(1H-indol-2-yl)-1,3,4-oxadiazol-2-yl]sulfonyl}methyl)-5-(4-chloro-3,5-dimethoxyphenyl)-1,2,4-oxadiazole and 3-({[5-(1H-indol-2-yl)-1,3,4-oxadiazol-2-yl]sulfonyl}methyl)-5-(4-chlorophenyl)-1,2,4-oxadiazole were more active than erlotinib, while compound 3-({[5-(1H-indol-2-yl)-1,3,4-oxadiazol-2-yl]sulfonyl}methyl)-5-(3,5-dimethoxyphenyl)-1,2,4-oxadiazole was comparable to the standard erlotinib. [ABSTRACT FROM AUTHOR]
- Published
- 2023
- Full Text
- View/download PDF
11. Sulfonyl fluoride synthesis via visible-light-mediated fluorosulfonylation of thianthrenium salts.
- Author
-
Shan, Lingling, Ma, Zhanhu, Ou, Caiyun, Cai, Yinxia, Ma, Yuyang, Guo, Yong, Ma, Xiaoyu, and Liu, Chao
- Subjects
- *
FLUORIDES , *SALTS , *SULFUR dioxide , *RADICALS (Chemistry) , *FLUORINATION , *SULFONYL compounds - Abstract
A visible-light-mediated fluorosulfonylation reaction of thianthrenium salts has been developed to prepare various sulfonyl fluorides with 1,4-diazabicyclo [2.2.2] octane bis (sulfur dioxide) (DABSO) as sulfonyl source and cheap KHF2 as fluorine source based on radical sulfur dioxide insertion and fluorination strategy. This operationally simple protocol proceeds with high functional-group tolerance under mild reaction conditions. [ABSTRACT FROM AUTHOR]
- Published
- 2023
- Full Text
- View/download PDF
12. The anti-amoebic potential of carboxamide derivatives containing sulfonyl or sulfamoyl moieties against brain-eating Naegleria fowleri.
- Author
-
Akbar, Noor, Siddiqui, Ruqaiyyah, El-Gamal, Mohammed I., Zaraei, Seyed-Omar, Alawfi, Bader S., and Khan, Naveed Ahmed
- Subjects
- *
NAEGLERIA fowleri , *CARBOXAMIDES , *MOIETIES (Chemistry) , *CYTOTOXINS , *ENDOTHELIAL cells , *SULFONYL compounds , *AMIDE derivatives - Abstract
Naegleria fowleri is a free-living thermophilic flagellate amoeba that causes a rare but life-threatening infection called primary amoebic meningoencephalitis (PAM), with a very high fatality rate. Herein, the anti-amoebic potential of carboxamide derivatives possessing sulfonyl or sulfamoyl moiety was assessed against pathogenic N. fowleri using amoebicidal, cytotoxicity and cytopathogenicity assays. The results from amoebicidal experiments showed that derivatives dramatically reduced N. fowleri viability. Selected derivatives demonstrated IC50 values at lower concentrations; 1j showed IC50 at 24.65 μM, while 1k inhibited 50% amoebae growth at 23.31 μM. Compounds with significant amoebicidal effects demonstrated limited cytotoxicity against human cerebral microvascular endothelial cells. Finally, some derivatives mitigated N. fowleri-instigated host cell death. Ultimately, this study demonstrated that 1j and 1k exhibited potent anti-amoebic activity and ought to be looked at in future studies for the development of therapeutic anti-amoebic pharmaceuticals. Further investigation is required to determine the clinical relevance of our findings. [ABSTRACT FROM AUTHOR]
- Published
- 2023
- Full Text
- View/download PDF
13. Progress in S–X Bond Formation by Halogen-Mediated Electrochemical Reactions.
- Author
-
Du, Juan, Du, Ya-long, and Gui, Qing-wen
- Subjects
- *
OXIDATIVE coupling , *BROMATES , *BIOACTIVE compounds , *RING formation (Chemistry) , *ORGANIC chemistry , *ORGANIC compounds , *ORGANOLEAD compounds , *ALKYL radicals - Abstract
First, the iodide anion is oxidized to molecular iodine at the anode, and then sulfonyl hydrazides B 13 b are utilized to generate sulfonyl radicals B I b for subsequent reactions. A possible reaction mechanism was proposed in which oxidation of the starting materials by bromine species (molecular bromine, hypobromite, bromate, perbromate and tribromide anions), generated by the anodic oxidation of the bromine anion, produced radical intermediates, the coupling of which led to the final products. Keywords: organosulfur compounds; electrosynthesis; halogen-mediated; eco-friendly; sulfonyl compounds; organic thiocyanates EN organosulfur compounds electrosynthesis halogen-mediated eco-friendly sulfonyl compounds organic thiocyanates 2799 2816 18 08/31/23 20230915 NES 230915 Graph 1 Introduction The significant influence of sulfur atoms on the electronic and physical properties of organic compounds has led to the widespread occurrence of sulfur functional groups in natural products, pharmaceuticals, and other biologically active compounds. The sulfonyl radical B I b is obtained by the oxidation of B 37a b with the iodine species obtained by oxidation of iodide at the anode. [Extracted from the article]
- Published
- 2023
- Full Text
- View/download PDF
14. Design and Synthesis of Novel 5-((3-(Trifluoromethyl)piperidin-1-yl)sulfonyl)indoline-2,3-dione Derivatives as Promising Antiviral Agents: In Vitro, In Silico, and Structure–Activity Relationship Studies.
- Author
-
Ezz Eldin, Rogy R., Saleh, Marwa A., Alwarsh, Sefat A., Rushdi, Areej, Althoqapy, Azza Ali, El Saeed, Hoda S., and Abo Elmaaty, Ayman
- Subjects
- *
STRUCTURE-activity relationships , *ANTIVIRAL agents , *SULFONYL compounds , *CHEMICAL synthesis , *VIRAL genes , *ISATIN - Abstract
Herein, a series of new isatin derivatives was designed and synthesized (1–9) as broad-spectrum antiviral agents. Consequently, the antiviral activities of the synthesized compounds (1–9) were pursued against three viruses, namely influenza virus (H1N1), herpes simplex virus 1 (HSV-1), and coxsackievirus B3 (COX-B3). In particular, compounds 9, 5, and 4 displayed the highest antiviral activity against H1N1, HSV-1, and COX-B3 with IC50 values of 0.0027, 0.0022, and 0.0092 µM, respectively. Compound 7 was the safest, with a CC50 value of 315,578.68 µM. Moreover, a quantitative PCR (real-time PCR) assay was carried out for the most relevant compounds. The selected compounds exhibited a decrease in viral gene expression. Additionally, the conducted in silico studies emphasized the binding affinities of the synthesized compounds and their reliable pharmacokinetic properties as well. Finally, a structure–antiviral activity relationship study was conducted to anticipate the antiviral activity change upon future structural modification. [ABSTRACT FROM AUTHOR]
- Published
- 2023
- Full Text
- View/download PDF
15. Surface modification of kevlar fabric with a novel sulfonyl aryl containing monomer and its influence on inter yarn friction.
- Author
-
Agarwal, Gaurav, Sharma, Indu, Prakash, Jyoti, Kumar, Pal Dinesh, and Verma, Sanjeev K
- Subjects
- *
POLYPHENYLENETEREPHTHALAMIDE , *YARN , *IMPACT response , *MONOMERS , *ARYL group , *ETHYL esters , *SULFONYL compounds - Abstract
The ballistic impact response of Kevlar textiles is significantly influenced by the friction between the yarns. It increases the dissipation of energy when yarns begin to displace relative to one another and it also results in to transfer of load to a larger area during ballistic impacts. In the present work, a novel sulfonyl aryl group containing monomer acrylic acid-2-(toluene sulphonyl amine)-ethyl ester (AATSAEE) was synthesized by a three-step process with ethanol amine and p-toluene sulfonic acid as starting material. The monomer was homopolymerized and grafted on Kevlar fabric by UV-induced free radical polymerization technique. Benzoyl peroxide (BPO) was used as initiator. Utilizing spectroscopic and thermal gravimetric methods, the monomer, precursor, and the homopolymer were characterized. The yarn pull-out tests on unmodified and AATSAEE grafted Kevlar fabrics were performed on Universal Tensile Tester at a steady speed of the upper jaw of 50 cm min−1. Increases in yarn pull out force have been noted with grafting of AATSAEE on Kevlar fabric. The peak force increases around 284% with grafting which indicates an increase in friction forces. When these yarns start to move apart from one another due to friction factors, the fabric's energy dissipation increases and it may results in to increase in energy absorption at the time of ballistic impacts. [ABSTRACT FROM AUTHOR]
- Published
- 2023
- Full Text
- View/download PDF
16. Enhancement of Fluorescence Emission Intensity in a Sulfonyl Hydrazide Derivative of tri(biphenyl‐4‐yl)amine via Solid‐state Grinding with Various Metal Salts: Combined Experimental and Computational Studies.
- Author
-
Mahto, Amit Kumar, Kuldeep, Barik, Sahadev, Gajula, Ramesh Kumar, Sarkar, Moloy, and Prakash, M. Jaya
- Subjects
- *
METAL grinding & polishing , *SALT crystals , *SULFONYL group , *FLUORESCENCE , *CRYSTAL surfaces , *HYDRAZIDES , *SULFONYL compounds - Abstract
Solid‐state fluorescent materials are in huge demand owing to their potential applications in sensors, imaging, and LEDs. The molecular aggregations in the solid state limit their usage in practical applications. Typically, J‐aggregates show enhanced emission, while H‐aggregates show quenching in the solid state. Few supramolecular approaches (like creating hydrogen bonds) were developed to disturb the π–π and other supramolecular interactions in solid‐state H‐aggregates. Herein, we are reporting a p‐toulenesulfonyl hydrazide derivative of tri(biphenyl‐4‐yl)amine (TBA‐THZ) in the solid state showed negligible emission while grinding with M+X− (M+=alkali and alkali earth metal) salts showed enhanced emission. Existing supramolecular interactions were disturbed by dipole‐ion interactions between S=O⋅⋅⋅M+. The micro/nanometer‐sized salt crystal particles serve as templates for the TBA‐THZ molecules, and in the broad sense, the salt crystal surfaces act as a "solid‐state solvent." The TBA‐THZ ground with various metal salts showed varied emission intensities; the BaCl2 ⋅ 2H2O salt ground sample exhibited the maximum emission intensity. The KPF6+18‐Crown‐6 sample showed 84 times enhanced emission than the pristine TBA‐THZ. The role of 18‐crown‐6 ether was observed as a donor type for K+ ions. The expected S=O⋅⋅⋅K+ dipole‐ion interactions were elucidated through FT‐IR and computational modelling. The slight change in emission wavelength to the higher side after grinding with metal salt indicates that dipole‐ion interactions might slightly modify the chromophore's electronic structure, encouraging radiative decay and higher emission intensity. In contrast, a similar molecule, TBA‐PH, with no sulfonyl functional group, was silent in emission intensity. The TBA‐PH solid has no significant emission even after grinding with metal salts. The emission capacity of the TBA‐THZ salt‐ground powder remained unchanged at higher temperatures and in a highly humid environment. The fluorescent active salt ground matrix of the TBA‐THZ responded admirably to HCl acid fumes and was regenerated upon exposure to ammonia vapours. [ABSTRACT FROM AUTHOR]
- Published
- 2023
- Full Text
- View/download PDF
17. Spectrophotmetric Determination of Dissociation Constanst of Isoniazid and Its Sulfonyl Derivatives.
- Author
-
Zafar, Shaista, Akhtar, Shamim, Ali, Mohsin, Ali, Syed Imran, Mushtaq, Nausheen, Ahmed, Ahsaan, and Naeem, Sabahat
- Subjects
- *
ANTITUBERCULAR agents , *ISONIAZID , *DRUG development , *SULFONYL compounds , *TRICHLOROPHENOL - Abstract
Among the physicochemical properties of drugs, dissociation constant (pKa) is the most important parameter for the design and development of new and existing drug molecules. We report for the first time, the experimental determination of dissociation constant (pKa) for a frontline anti-tubercular drug isoniazid. Besides, pKa values of the two of its newly synthesized sulfonyl derivatives, N′-[(2,4,6-trimethylbenzene)sulfonyl]pyridine-4-carbohydrazide (SZ-I), N′-[(4-bromobenzene)sulfonyl]pyridine-4-carbohydrazide (SZ-II) were also determined. The approach adopted was UV–Visible spectrophotometry which is an established analytical method known for its accuracy and reproducibility. The spectrophotometric analysis was performed by measuring the absorbance values at various pH and the pKa values were then calculated using Henderson-Hasselbalch equation. The pKa values were found to be 3.0, 3.55 and 3.43 for Isoniazid (INH) and its sulfonyl derivatives SZ-I and SZ-II, respectively. [ABSTRACT FROM AUTHOR]
- Published
- 2023
- Full Text
- View/download PDF
18. Photoenzymatic Hydrosulfonylation for the Stereoselective Synthesis of Chiral Sulfones.
- Author
-
Chen, Xiaoyang, Zheng, Dannan, Jiang, Linye, Wang, Zhiguo, Duan, Xinyu, Cui, Dong, Liu, Shuang, Zhang, Yuan, Yu, Xiaomin, Ge, Jingyan, and Xu, Jian
- Subjects
- *
SULFONYL compounds , *SULFONES , *REDUCTASES , *METAL complexes , *ENZYMES - Abstract
Chiral sulfones are recurrent motifs in pharmaceuticals and bioactive molecules. Although chemical methods have been developed to afford α‐ or β‐ chiral sulfones, these protocols rely heavily on the pre‐synthesis of structurally complicated starting materials and chiral metal complexes. Herein, we described a photoenzymatic approach for the radical‐mediated stereoselective hydrosulfonylation. Engineered variants of ene reductases provide efficient biocatalysts for this transformation, enabling to achieve a series of β‐chiral sulfonyl compounds with high yields (up to 92 %) and excellent e.r. values (up to 99 : 1). [ABSTRACT FROM AUTHOR]
- Published
- 2023
- Full Text
- View/download PDF
19. Photoenzymatic Hydrosulfonylation for the Stereoselective Synthesis of Chiral Sulfones.
- Author
-
Chen, Xiaoyang, Zheng, Dannan, Jiang, Linye, Wang, Zhiguo, Duan, Xinyu, Cui, Dong, Liu, Shuang, Zhang, Yuan, Yu, Xiaomin, Ge, Jingyan, and Xu, Jian
- Subjects
- *
SULFONYL compounds , *SULFONES , *REDUCTASES , *METAL complexes , *ENZYMES - Abstract
Chiral sulfones are recurrent motifs in pharmaceuticals and bioactive molecules. Although chemical methods have been developed to afford α‐ or β‐ chiral sulfones, these protocols rely heavily on the pre‐synthesis of structurally complicated starting materials and chiral metal complexes. Herein, we described a photoenzymatic approach for the radical‐mediated stereoselective hydrosulfonylation. Engineered variants of ene reductases provide efficient biocatalysts for this transformation, enabling to achieve a series of β‐chiral sulfonyl compounds with high yields (up to 92 %) and excellent e.r. values (up to 99 : 1). [ABSTRACT FROM AUTHOR]
- Published
- 2023
- Full Text
- View/download PDF
20. The synthesis of biologically active 1-sulfonyl-1, 2, 3-triazoles from sulfonyl azides and alkynes: a focus review.
- Author
-
Kadhim, Mustafa M., Abdulkareem Mahmood, Evan, Poor Heravi, Mohammad Reza, Soleimani-Amiri, Somayeh, Ebadi, Abdol Ghaffar, and Vessally, Esmail
- Subjects
- *
SULFONYL azides , *ALKYNES , *TRIAZOLE derivatives , *COPPER catalysts , *RING formation (Chemistry) , *SULFONYL compounds - Abstract
In this review, we spotlight the methods for the direct synthesis of synthetically and biologically important 1-sulfonyl-1, 2, 3-triazoles via [3+2] cycloaddition between easily available terminal alkynes and sulfonyl azides. The review is divided into two major sections. The first section focuses exclusively on the synthesis of 1-(N-sulfonyl)-4-substituted 1,2,3-triazoles, while the second section will discuss preparation of 1-(N-sulfonyl)-5-substituted 1,2,3-triazole derivatives. [ABSTRACT FROM AUTHOR]
- Published
- 2023
- Full Text
- View/download PDF
21. Radical bicyclization of 1,6-enynes with sulfonyl hydrazides by the use of TBAI/TBHP in the aqueous phase.
- Author
-
Liu, Fa-Liang, Mei, Lan, Wang, Ling-Tao, Zhou, Yu, Tang, Keqi, Li, Ting, Yi, Rongnan, and Wei, Wen-Ting
- Subjects
- *
HYDRAZIDES , *SULFONYL compounds , *IODIDES - Abstract
A novel 5-exo-dig/6-endo-trig bicyclization of 1,6-enynes with sulfonyl hydrazides in the aqueous phase using the cheap and available tetrabutylammonium iodide (TBAI)–tert-butyl hydroperoxide (TBHP) combined system is reported. The resulting reaction of diverse nitrogen- and oxygen-polyheterocycles displays high chemical selectivity, high step-economy, and a moderate substrate scope. Moreover, iodosulfonylation can be realized by modulating the structure of the 1,6-enynes. [ABSTRACT FROM AUTHOR]
- Published
- 2023
- Full Text
- View/download PDF
22. Interface stabilization via lithium bis(fluorosulfonyl)imide additive as a key for promoted performance of graphite‖LiCoO2 pouch cell under −20 ○C.
- Author
-
Pham, Hieu Quang, Chung, Gyeong Jun, Han, Jisoo, Hwang, Eui-Hyung, Kwon, Young-Gil, and Song, Seung-Wan
- Subjects
- *
SUPERIONIC conductors , *ENERGY storage , *FLUOROETHYLENE , *SULFONYL compounds , *LITHIUM-ion batteries , *INTERFACIAL resistance , *ORGANIC compounds ,COLD regions - Abstract
The effects of lithium bis(fluorosulfonyl)imide, Li[N(SO2F)2] (LiFSI), as an additive on the low-temperature performance of graphite ‖ LiCoO2 pouch cells are investigated. The cell, which includes 0.2M LiFSI salt additive in the 1M lithium hexafluorophosphate (LiPF6)-based conventional electrolyte, outperforms the one without additive under −20 °C and high charge cutoff voltage of 4.3 V, delivering higher discharge capacity and promoted rate performance and cycling stability with the reduced change in interfacial resistance. Surface analysis results on the cycled LiCoO2 cathodes and cycled graphite anodes extracted from the cells provide evidence that a LiFSI-induced improvement of high-voltage cycling stability at low temperature originates from the formation of a less resistive solid electrolyte interphase layer, which contains plenty of LiFSI-derived organic compounds mixed with inorganics that passivate and protect the surface of the cathode and anode from further electrolyte decomposition and promotes Li+ ion-transport kinetics despite the low temperature, inhibiting Li metal-plating at the anode. The results demonstrate the beneficial effects of the LiFSI additive on the performance of a lithium-ion battery for use in battery-powered electric vehicles and energy storage systems in cold climates and regions. [ABSTRACT FROM AUTHOR]
- Published
- 2020
- Full Text
- View/download PDF
23. Structural analysis of ionic liquids with symmetric and asymmetric fluorinated anions.
- Author
-
Zhao, Man, Wu, Boning, Lall-Ramnarine, Sharon I., Ramdihal, Jasodra D., Papacostas, Kristina A., Fernandez, Eddie D., Sumner, Rawlric A., Margulis, Claudio J., Wishart, James F., and Castner, Edward W.
- Subjects
- *
LIQUID analysis , *IONIC liquids , *ASYMMETRIC dimethylarginine , *MOLECULAR dynamics , *ANIONS , *SULFONYL compounds , *IONIC structure - Abstract
Ionic liquids (ILs) with relatively low viscosities and broad windows of electrochemical stability are often constructed by pairing asymmetric cations with bisfluorosulfonylimide (FSI−) or bistriflimide ( NTf 2 − ) anions. In this work, we systematically studied the structures of ILs with these anions and related perfluorobis-sulfonylimide anions with asymmetry and/or longer chains: (fluorosulfonyl)(trifluoromethylsulfonyl)imide ( B S I 0 , 1 − ), bis(pentafluoroethylsulfonyl)imide (BETI−), and (trifluoromethylsulfonyl) (nonafluorobutylsulfonyl)imide ( B S I 1 , 4 − ) using high energy X-ray scattering and molecular dynamics simulation methods. 1-alkyl-3-methylimidazolium cations with shorter (ethyl, Im 2 , 1 + ) and longer (octyl, Im 1 , 8 + ) hydrocarbon chains were selected to examine how the sizes of nonpolar hydrocarbon and fluorous chains affect IL structures and properties. In comparison with these, we also computationally explored the structure of ionic liquids with anions having longer fluorinated tails. [ABSTRACT FROM AUTHOR]
- Published
- 2019
- Full Text
- View/download PDF
24. Electrochemical Oxidation Involving Sulfonyl Hydrazine for the Synthesis of 2‐Sulfonyl Quinolines/Pyridines.
- Author
-
Wang, Luyao, Ning, Zhitao, Xu, Zheng, Liu, Ruikai, and Du, Zhengyin
- Subjects
- *
HYDRAZINES , *HYDRAZINE , *POTASSIUM carbonate , *QUINOLINE derivatives , *PYRIDINE derivatives , *QUINOLINE , *HYDRAZIDES , *SULFONYL compounds - Abstract
A mild electrochemical method was developed for the direct C2 sulfonylation of heteroaromatic N‐oxides with sulfonyl hydrazides to obtain a serial of 2‐sulfonyl quinoline/pyridine derivatives. The method has simple conditions, using potassium carbonate as base, CH3CN/H2O (9 : 1) as solvent, and reacting for 3 h under 15 mA current to prepare expected products. [ABSTRACT FROM AUTHOR]
- Published
- 2023
- Full Text
- View/download PDF
25. A study on the viscosity, density, and derivative properties of 1-alkyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl)imides with benzo-15-crown-5 binary mixtures.
- Author
-
Tian, Ju, Tang, Qi, Zhang, Yongshen, Shu, Yuzhen, Zhang, Lihua, and Zheng, Weiming
- Subjects
- *
BINARY mixtures , *IMIDES , *VISCOSITY , *LIQUID mixtures , *IONIC liquids , *MOLE fraction , *SULFONYL compounds - Abstract
The essential factors that affect the interfacial mass transfer rate of crown ether–ionic liquid systems are studied by examining the physicochemical properties of mixtures of ionic liquids with benzo-15-crown-5. In the present work, the 1-alkyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl)imides ionic liquids ([C2MIm][NTf2], [C3MIm][NTf2], [C4MIm][NTf2], and [C5MIm][NTf2]) are adopted as the solvent and benzo-15-crown-5 is used as the solute. A series of binary mixtures of the ionic liquid and benzo-15-crown-5, with different molar fractions of ionic liquids, is formulated by the weight method. The viscosity and density are determined for four binary mixtures of ionic liquid and benzo-15-crown-5 at atmospheric pressure in a temperature range of 298.15 to 343.15 K. The values obtained for viscosity and density are fitted with empirical equations, and the energy barrier, a -constant, and the isobaric thermal expansion coefficient are all calculated. Interactions between the ionic liquid and the solute benzo-15-crown-5 are analyzed, and the above properties are discussed by comparison with systems in which different solutes are present in the same ionic liquid. It is found that interactions between the ionic liquid and benzo-15-crown-5 in the mixtures are more intense than in mixed systems composed of ionic liquids and other solutes. [ABSTRACT FROM AUTHOR]
- Published
- 2023
- Full Text
- View/download PDF
26. Divergent Reaction of Allenoates: Synthesis of Polysubstituted Pyrazoles and N‐Alkylated Hydrazones.
- Author
-
Rajai‐Daryasarei, Saideh, Rominger, Frank, Reza Bijanzadeh, Hamid, and Balalaie, Saeed
- Subjects
- *
HYDRAZONES , *PYRAZOLES , *HYDRAZONE derivatives , *SULFONYL compounds , *HYDRAZIDES , *AROMATIC aldehydes - Abstract
A strategy for the divergent synthesis of polysubstituted pyrazoles and N‐alkylated hydrazone derivatives through three‐component reaction of aromatic aldehydes, aryl sulfonyl hydrazides, and allenoates under the mild reaction conditions is described. Both products can be obtained by changing the reaction base. [ABSTRACT FROM AUTHOR]
- Published
- 2022
- Full Text
- View/download PDF
27. A Novel Reaction of Sulfonyl Azides with Phosphine Sulfides.
- Author
-
Filimonov, V. O., Il'kin, V. G., Seliverstova, E. A., and Bakulev, V. A.
- Subjects
- *
SULFONYL azides , *SULFIDES , *PHOSPHINE , *ORGANOPHOSPHORUS compounds , *SULFONYL compounds , *SULFONAMIDES , *PHOSPHINES - Abstract
(4-Methoxyphenyl)di(pyrrolidin-1-yl)phosphine sulfides were synthesized by the reaction of Lausson's reagent with cyclic amines. It was shown for the first time that phosphine sulfides react with arenesulfonyl azides in 1,4-dioxane under reflux with the elimination of nitrogen and elemental sulfur to form previously unknown dicycloaminophosphoranylidene sulfonamides. [ABSTRACT FROM AUTHOR]
- Published
- 2023
- Full Text
- View/download PDF
28. Low-energy electron-induced decomposition of 5-trifluoromethanesulfonyl-uracil: A potential radiosensitizer.
- Author
-
Ameixa, J., Arthur-Baidoo, E., Meißner, R., Makurat, S., Kozak, W., Butowska, K., Ferreira da Silva, F., Rak, J., and Denifl, S.
- Subjects
- *
RADIATION-sensitizing agents , *TRIFLUOROMETHANESULFONYL compounds , *URACIL , *CHEMICAL decomposition , *LOW energy electron diffraction , *DISSOCIATION (Chemistry) , *DEHYDROGENATION , *SCISSION (Chemistry) - Abstract
5-trifluoromethanesulfonyl-uracil (OTfU), a recently proposed radiosensitizer, is decomposed in the gas-phase by attachment of low-energy electrons. OTfU is a derivative of uracil with a triflate (OTf) group at the C5-position, which substantially increases its ability to undergo effective electron-induced dissociation. We report a rich assortment of fragments formed upon dissociative electron attachment (DEA), mostly by simple bond cleavages (e.g., dehydrogenation or formation of OTf−). The most favorable DEA channel corresponds to the formation of the triflate anion alongside with the reactive uracil-5-yl radical through the cleavage of the O–C5 bond, particularly at about 0 eV. Unlike for halouracils, the parent anion was not detected in our experiments. The experimental findings are accounted by a comprehensive theoretical study carried out at the M06-2X/aug-cc-pVTZ level. The latter comprises the thermodynamic thresholds for the formation of the observed anions calculated under the experimental conditions (383.15 K and 3 × 10−11 atm). The energy-resolved ion yield of the dehydrogenated parent anion, (OTfU–H)−, is discussed in terms of vibrational Feshbach resonances arising from the coupling between the dipole bound state and vibrational levels of the transient negative ion. We also report the mass spectrum of the cations obtained through ionization of OTfU by electrons with a kinetic energy of 70 eV. The current study endorses OTfU as a potential radiosensitizer agent with possible applications in radio-chemotherapy. [ABSTRACT FROM AUTHOR]
- Published
- 2018
- Full Text
- View/download PDF
29. Novel 7-Chloro-(4-thioalkylquinoline) Derivatives: Synthesis and Antiproliferative Activity through Inducing Apoptosis and DNA/RNA Damage.
- Author
-
Gutiérrez, Joyce E., Fernandez-Moreira, Esteban, Rodríguez, Miguel A., Mijares, Michael R., De Sanctis, Juan Bautista, Gurská, Soňa, Džubák, Petr, Hajdůch, Marián, Bruno-Colmenarez, Julia, Rojas, Luis, Deffieux, Denis, Pouységu, Laurent, Quideau, Stéphane, Charris, Jaime, and Ramírez, Hegira
- Subjects
- *
DNA synthesis , *DNA , *RNA , *CANCER cells , *CELL lines , *SULFONYL compounds - Abstract
A series of 78 synthetic 7-chloro-(4-thioalkylquinoline) derivatives were investigated for cytotoxic activity against eight human cancer as well as 4 non-tumor cell lines. The results showed, with some exceptions, that sulfanyl 5–40 and sulfinyl 41–62 derivatives exhibited lower cytotoxicity for cancer cell lines than those of well-described sulfonyl N-oxide derivatives 63–82. As for compound 81, the most pronounced selectivity (compared against BJ and MRC-5 cells) was observed for human cancer cells from HCT116 (human colorectal cancer with wild-type p53) and HCT116p53−/− (human colorectal cancer with deleted p53), as well as leukemia cell lines (CCRF-CEM, CEM-DNR, K562, and K562-TAX), lung (A549), and osteosarcoma cells (U2OS). A good selectivity was also detected for compounds 73 and 74 for leukemic and colorectal (with and without p53 deletion) cancer cells (compared to MRC-5). At higher concentrations (5 × IC50) against the CCRF-CEM cancer cell line, we observe the accumulation of the cells in the G0/G1 cell phase, inhibition of DNA and RNA synthesis, and induction of apoptosis. In addition, X-ray data for compound 15 is being reported. These results provide useful scientific data for the development of 4-thioalkylquinoline derivatives as a new class of anticancer candidates. [ABSTRACT FROM AUTHOR]
- Published
- 2022
- Full Text
- View/download PDF
30. High-efficiency synthesis of sulfenamides and disulfides by electrochemical dehydrogenative coupling.
- Author
-
Zhang, Tong, Wang, Ruke, Ma, Linzheng, Liu, Jing, Sun, Jifu, and Wang, Bo
- Subjects
- *
SULFONYL chlorides , *DISULFIDES , *POTASSIUM iodide , *POISONS , *SUSTAINABLE chemistry , *THIOLS , *NUCLEOPHILES , *SULFONYL compounds - Abstract
Catalytic dehydrogenative coupling of thiols with amines to produce sulfenamides and disulfides is an important reaction in the industry. Classical synthesis of sulfenamides involves the reaction between amine nucleophiles and sulfonyl chlorides, which are not widely available, toxic and unstable, and the reaction requires a combination of oxidizing and chlorinating reagents. Here we decribe an environmentally benign protocol for the efficient electrochemical dehydrogenative coupling of thiols with amines or thiols to form compounds possessing S–N or S–S bonds. We used potassium iodide as electrocatalyst in methanol for a greener reaction. The reaction operates under ambient conditions in the absence of oxidants, acids/bases or toxic/explosive electrolytes. Results show that most produced sulfenamides and disulfides are generated in yields up to 99%. [ABSTRACT FROM AUTHOR]
- Published
- 2022
- Full Text
- View/download PDF
31. Convenient Synthesis of Some New Thiophene, Pyrazole, and Thiazole Derivatives Bearing Biologically Active Sulfonyl Guanidine Moiety.
- Author
-
Fouad, Sawsan A., El-Gendey, Marwa S., Ahmed, Entsar M., Hessein, Sadia A., Ammar, Yousry A., and Zaki, Yasser H.
- Subjects
- *
GUANIDINE derivatives , *THIAZOLES , *THIAZOLE derivatives , *SULFONYL compounds , *THIOPHENES , *PYRAZOLES , *GUANIDINE , *MOIETIES (Chemistry) - Abstract
The synthesis and characterization of a variety of novel heterocyclic compounds bearing the pharmacophore N-carbamimidoylsulfamoyl moiety that are relevant to antibacterial and antifungal activities are described. All the newly synthesized compounds have been characterized on the basis of IR, 1H MR and 13C NMR spectral data as well as physical data. The synthesized compounds, except thiophene 10, were tested against six standard microbial pathogens, and the antimicrobial activity of these compounds was evaluated according to the microdilution method. Most of the newly tested derivatives showed good to excellent antimicrobial activity when applied to MIC/MBC and MIC/MFC values. [ABSTRACT FROM AUTHOR]
- Published
- 2022
- Full Text
- View/download PDF
32. Synthesis of Thiosulfonates by I2/TBHP‐mediated the Ring‐opening/coupling Reaction of Benzothiazole.
- Author
-
Chen, Tianpeng, Tao, Yuhui, Wu, Ziliang, Xu, Xiaoliang, and Cheng, Dongping
- Subjects
- *
BENZOTHIAZOLE , *HYDRAZIDES , *HYDROPEROXIDES , *SULFONYL compounds - Abstract
A novel I2/TBHP (tert‐Butyl hydroperoxide)‐mediated the ring‐opening/coupling reaction of benzothiazole with sulfonyl hydrazides is disclosed. Various aryl, heteraryl and alkyl sulfonyl hydrazides are applied for the reaction and the corresponding thiosulfonates are obtained in moderate to good yields. It provides a mild and convenient way for the synthesis of thiosulfonates. [ABSTRACT FROM AUTHOR]
- Published
- 2022
- Full Text
- View/download PDF
33. Differential Dihydrofunctionalization: A Dual Catalytic Three‐Component Coupling of Alkynes, Alkenyl Bromides, and Pinacolborane.
- Author
-
Baumann, James E. and Lalic, Gojko
- Subjects
- *
ALKYNES , *BORONIC esters , *SILYL ethers , *PALLADIUM catalysts , *HALOALKANES , *ARYL halides , *SULFONYL compounds - Abstract
A new method for differential dihydrofunctionalization of terminal alkynes enables the synthesis of allylic boronate esters through reductive three‐component coupling of terminal alkynes, alkenyl bromides, and pinacolborane. The transformation is promoted by cooperative action of a copper/palladium catalyst system and results in hydrofunctionalization of both π‐bonds of an alkyne. The synthesis of allylic boronate esters can be accomplished in the presence of a wide range of functional groups, including, esters, nitriles, alkyl halides, sulfonyl esters, acetals, protected terminal alkynes, aryl halides, and silyl ethers. Mechanistic experiments reveal the importance of subtle ligand effects on the performance of the palladium co‐catalyst. [ABSTRACT FROM AUTHOR]
- Published
- 2022
- Full Text
- View/download PDF
34. Differential Dihydrofunctionalization: A Dual Catalytic Three‐Component Coupling of Alkynes, Alkenyl Bromides, and Pinacolborane.
- Author
-
Baumann, James E. and Lalic, Gojko
- Subjects
- *
ALKYNES , *BORONIC esters , *SILYL ethers , *PALLADIUM catalysts , *HALOALKANES , *ARYL halides , *SULFONYL compounds - Abstract
A new method for differential dihydrofunctionalization of terminal alkynes enables the synthesis of allylic boronate esters through reductive three‐component coupling of terminal alkynes, alkenyl bromides, and pinacolborane. The transformation is promoted by cooperative action of a copper/palladium catalyst system and results in hydrofunctionalization of both π‐bonds of an alkyne. The synthesis of allylic boronate esters can be accomplished in the presence of a wide range of functional groups, including, esters, nitriles, alkyl halides, sulfonyl esters, acetals, protected terminal alkynes, aryl halides, and silyl ethers. Mechanistic experiments reveal the importance of subtle ligand effects on the performance of the palladium co‐catalyst. [ABSTRACT FROM AUTHOR]
- Published
- 2022
- Full Text
- View/download PDF
35. Synthesis of Poly(thioester sulfonamide)s via the Ring‐Opening Copolymerization of Cyclic Thioanhydride with N‐Sulfonyl Aziridine Using Mild Phosphazene Base.
- Author
-
Song, Peng‐Duo, Xia, Lei, Nie, Xuan, Chen, Guang, Wang, Fei, Zhang, Ze, Hong, Chun‐Yan, and You, Ye‐Zi
- Subjects
- *
COPOLYMERIZATION , *SULFONAMIDES , *POLYMER structure , *MOLECULAR weights , *ANHYDRIDES , *SULFONYL compounds - Abstract
Providing access to diverse polymer structures is highly desirable, which helps to explore new polymer materials. Poly(thioester sulfonamide)s, combining both the advantages of thioesters and amides, however, are rarely available in polymer chemistry. Here, the ring‐opening copolymerization (ROCOP) of cyclic thioanhydride with N‐sulfonyl aziridine using mild phosphazene base, resulting in well‐defined poly(thioester sulfonamide)s with highly alternative structures, high yields, and controlled molecular weights, is reported. Additionally, benefiting from the mild catalytic process, this ROCOP can be combined with ROCOP of N‐sulfonyl aziridines with cyclic anhydrides to produce novel block copolymers. [ABSTRACT FROM AUTHOR]
- Published
- 2022
- Full Text
- View/download PDF
36. Diversification of Aryl Sulfonyl Compounds through Ligand‐Controlled meta‐ and para‐C−H Borylation.
- Author
-
Wang, Yajun, Chang, Wenju, Qin, Shengmeng, Ang, Han, Ma, Jiawei, Lu, Shuo, and Liang, Yong
- Subjects
- *
SULFONYL compounds , *AROMATIC compounds , *BORYLATION , *IRIDIUM catalysts , *ORGANIC synthesis , *SULFONES - Abstract
Aryl sulfones and aryl sulfonamides are of great importance in organic synthesis and medicinal chemistry. Although ortho‐C−H functionalization of aryl sulfonyl compounds has been extensively explored, the functionalization of remote meta‐ and para‐C−H bonds is very rare. Herein, we report a tunable meta‐ and para‐selective C−H borylation of aryl sulfonyl compounds enabled by computationally designed ligands and iridium catalyst. This method is capable of accommodating a broad range of substrates under mild reaction conditions. Gram‐scale preparation can be achieved with iridium catalyst loading as low as 0.1 mol%. As the introduced boronate group can be easily converted into many other groups, our method provides a general solution to installing functional groups at either meta‐ or para‐position of aryl sulfones and aryl sulfonamides with good to excellent selectivity. [ABSTRACT FROM AUTHOR]
- Published
- 2022
- Full Text
- View/download PDF
37. Diversification of Aryl Sulfonyl Compounds through Ligand‐Controlled meta‐ and para‐C−H Borylation.
- Author
-
Wang, Yajun, Chang, Wenju, Qin, Shengmeng, Ang, Han, Ma, Jiawei, Lu, Shuo, and Liang, Yong
- Subjects
- *
SULFONYL compounds , *AROMATIC compounds , *BORYLATION , *IRIDIUM catalysts , *ORGANIC synthesis , *SULFONES - Abstract
Aryl sulfones and aryl sulfonamides are of great importance in organic synthesis and medicinal chemistry. Although ortho‐C−H functionalization of aryl sulfonyl compounds has been extensively explored, the functionalization of remote meta‐ and para‐C−H bonds is very rare. Herein, we report a tunable meta‐ and para‐selective C−H borylation of aryl sulfonyl compounds enabled by computationally designed ligands and iridium catalyst. This method is capable of accommodating a broad range of substrates under mild reaction conditions. Gram‐scale preparation can be achieved with iridium catalyst loading as low as 0.1 mol%. As the introduced boronate group can be easily converted into many other groups, our method provides a general solution to installing functional groups at either meta‐ or para‐position of aryl sulfones and aryl sulfonamides with good to excellent selectivity. [ABSTRACT FROM AUTHOR]
- Published
- 2022
- Full Text
- View/download PDF
38. An Aminative Rearrangement of O‐(Arenesulfonyl)hydroxylamines: Facile Access to ortho‐Sulfonyl Anilines.
- Author
-
Morrill, Charlotte, Gillespie, James E., and Phipps, Robert J.
- Subjects
- *
ANILINE , *REARRANGEMENTS (Chemistry) , *SULFONATION , *SULFONYL compounds - Abstract
Ortho‐sulfonyl anilines are important building blocks for a range of applications. We report the discovery of an aromatic rearrangement reaction of O‐(arenesulfonyl)hydroxylamines which leads directly to ortho‐sulfonyl anilines through formation of a new C−N bond with excellent levels of regiocontrol for the ortho position(s) over all others. We establish that the rearrangement is proceeding through an intermolecular mechanism and propose that the regiocontrol observed is the result of attractive non‐covalent interactions occurring during the C−N bond‐forming step. Importantly, this method is complementary to classical aniline sulfonation in terms of the variously substituted regioisomers that can be obtained and it is also applicable to O‐(benzylsulfonyl) hydroxylamines. [ABSTRACT FROM AUTHOR]
- Published
- 2022
- Full Text
- View/download PDF
39. An Aminative Rearrangement of O‐(Arenesulfonyl)hydroxylamines: Facile Access to ortho‐Sulfonyl Anilines.
- Author
-
Morrill, Charlotte, Gillespie, James E., and Phipps, Robert J.
- Subjects
- *
ANILINE , *REARRANGEMENTS (Chemistry) , *SULFONATION , *SULFONYL compounds - Abstract
Ortho‐sulfonyl anilines are important building blocks for a range of applications. We report the discovery of an aromatic rearrangement reaction of O‐(arenesulfonyl)hydroxylamines which leads directly to ortho‐sulfonyl anilines through formation of a new C−N bond with excellent levels of regiocontrol for the ortho position(s) over all others. We establish that the rearrangement is proceeding through an intermolecular mechanism and propose that the regiocontrol observed is the result of attractive non‐covalent interactions occurring during the C−N bond‐forming step. Importantly, this method is complementary to classical aniline sulfonation in terms of the variously substituted regioisomers that can be obtained and it is also applicable to O‐(benzylsulfonyl) hydroxylamines. [ABSTRACT FROM AUTHOR]
- Published
- 2022
- Full Text
- View/download PDF
40. Post-polymerization modification of polypropylene with different functional groups utilizing non-catalytic C–H insertion of sulfonyl azide.
- Author
-
Ko, Ju Yeon, Appa, Rama Moorthy, Oh, Sevin, Son, Nakyung, and Hong, Sung Chul
- Subjects
- *
FUNCTIONAL groups , *CARBONYL group , *CARBOXYL group , *SULFONYL compounds , *X-ray diffraction , *POLYPROPYLENE , *ACRYLIC paint - Abstract
This study presents a comprehensive investigation into the preparation of functionalized polypropylene (PP) with different functional groups, such as amino-, hydroxyl-, acetamido-, and carboxyl-groups, utilizing efficient C –H insertion capability of sulfonyl azide (SA) compounds with the functional groups. The reactive melt mixing of PP and the SA compounds was performed at temperatures determined by the decomposition temperatures of the SA groups, followed by purification processes to remove unreacted SA compounds, confirming the establishment of stable covalent linkages between the SA compounds and PP chains. Grafting efficiency (GE) values were determined using FT-IR spectroscopy, showcasing efficient grafting of the SA compounds onto PP chains with GE values ranging from 60 % to 70 %. Remarkably, SA compound with carboxyl functional group exhibited an exceptionally high GE value of ∼90 %, likely attributed to its electron-withdrawing carbonyl group. XRD analyses, thermal analyses, morphological analyses of cryogenically fractured modified PPs and mechanical property analyses revealed successful incorporation of SA compounds into PP chains with relatively low sensitivity of the crystal structure of the modified PPs to the incorporated SA compounds. Hydrophilicity assessments revealed improved paint adhesion capabilities of the modified PP surfaces, highlighting the potential for the tailored surface modification strategies to enhance material characteristics. [Display omitted] • A method for introducing functional groups onto PP is demonstrated. • Sulfonyl azide compounds with various functional groups are used. • The method achieves high grafting efficiency values ranging from 60 % to 90 %. • The PPs exhibit enhanced hydrophilicity and improved paint adhesion capabilities. • The potential of this method for tailoring surface properties of PP is highlighted. [ABSTRACT FROM AUTHOR]
- Published
- 2024
- Full Text
- View/download PDF
41. Access to Sulfocoumarins by Three‐Component Reaction of β‐Keto Sulfonyl Fluorides, Arynes, and DMF.
- Author
-
Huang, Yuan, Zhao, Xueyan, Chen, Dengfeng, Zheng, Yu, Luo, Jinyue, and Huang, Shenlin
- Subjects
- *
FLUORIDES , *SULFUR , *QUINONE , *SULFONYL compounds - Abstract
Sulfonyl fluorides have found diverse applications in multiple disciplines due to their reactivity and stability. Thus, exploiting the new reactivity of sulfonyl fluorides is of high importance to Sulfur (VI) Fluoride Exchange (SuFEx) chemistry. Reported herein is a three‐component reaction of β‐keto sulfonyl fluorides, arynes and DMF for the streamline synthesis of sulfocoumarins. The reaction proceeds by trapping of the in situ generated o‐quinone methides with β‐keto sulfonyl fluorides, followed by selective cyclization with sulfonyl fluorides. This strategy provides a new avenue to access diverse sulfocoumarins with under mild conditions. [ABSTRACT FROM AUTHOR]
- Published
- 2022
- Full Text
- View/download PDF
42. Triflic‐Acid‐Catalyzed Friedel‐Crafts Reaction for the Synthesis of Diaryl Sulfones.
- Author
-
Falconnet, Alban, Arndt, Jan‐Dirk, Hashmi, A. Stephen K., and Schaub, Thomas
- Subjects
- *
FRIEDEL-Crafts reaction , *SULFONYL chlorides , *SULFONES , *SULFONYL compounds , *ARYL chlorides , *SULFONE derivatives , *BORONIC acids , *HIGH temperatures - Abstract
The Friedel‐Crafts sulfonylation for the synthesis of diaryl sulfones derivatives was achieved by using triflic acid (TfOH) as the acidic catalyst with aryl sulfonyl chlorides and arenes at elevated temperatures. Different sulfones could be synthesized with this method in good to excellent yield and with high selectivity. In contrast to the previous methodology reported for this sulfonylation, the catalyst and the excess of arene could be easily recovered and re‐used in further batches. [ABSTRACT FROM AUTHOR]
- Published
- 2022
- Full Text
- View/download PDF
43. Synthesis of sulfone derivatives via palladium-catalyzed cross-coupling of benzyl trimethylammonium triflates and sulfonyl hydrazides.
- Author
-
Wan, Juelin, Yu, Weijie, Wang, Tao, and Luo, Jin
- Subjects
- *
SULFONE derivatives , *SULFONYL compounds , *HYDRAZIDES , *SULFONYL chlorides , *SULFONES , *FUNCTIONAL groups - Abstract
A palladium-catalyzed cross-coupling of benzyl trimethylammonium triflates and sulfonyl hydrazides for the synthesis of various benzyl sulfones is reported. This novel protocol shows widespread functional group tolerance, leading to the desired sulfones in moderate to excellent yields. [ABSTRACT FROM AUTHOR]
- Published
- 2022
- Full Text
- View/download PDF
44. Synthesis of Spirocyclic Cyclobutenes through Desulfinative Spirocyclisation of gem‐Bis(triflyl)cyclobutenes.
- Author
-
Hoshikawa, Shoki, Yanai, Hikaru, and Matsumoto, Takashi
- Subjects
- *
CYCLOBUTENES , *SULFONYL compounds , *SPIRO compounds - Abstract
A two‐step synthesis of less accessible spiro[cyclobutene‐1,9′‐fluorene] compounds from biaryl‐alkynes and 2‐(2‐fluoropyridin‐1‐ium‐1‐yl)‐1,1‐bis((trifluoromethyl)sulfonyl)ethan‐1‐ide, which serves as a potent precursor for outstandingly electrophilic Tf2C=CH2, has been developed. This synthetic methodology includes selective formation of gem‐bis(triflyl)cyclobutenes from biaryl‐alkynes and Tf2C=CH2 followed by desulfinative spirocyclisation mediated by 1,1,1,3,3,3‐hexafluoroisopropyl alcohol (HFIP). Besides, on the basis of the chameleonic reactivity of sulfone functionality, several derivatisations of triflylated spiro[cyclobutene‐1,9′‐fluorene] products have been successfully achieved. [ABSTRACT FROM AUTHOR]
- Published
- 2022
- Full Text
- View/download PDF
45. Synthesis, Spectroscopic Analysis, and In Vitro Anticancer Evaluation of 2-(Phenylsulfonyl)-2 H -1,2,3-triazole.
- Author
-
Salinas-Torres, Angélica, Portilla, Jaime, Rojas, Hugo, Becerra, Diana, and Castillo, Juan-Carlos
- Subjects
- *
SULFONYL group , *PHARMACEUTICAL chemistry , *NUCLEAR magnetic resonance spectroscopy , *CENTRAL nervous system , *MASS spectrometry , *SULFONYL compounds - Abstract
The 1,2,3-Triazole derivatives containing the sulfonyl group have proved their biological importance in medicinal chemistry and drug design. In this sense, we describe the regioselective synthesis of 2-(phenylsulfonyl)-2H-1,2,3-triazole 3 in good yield through a classical sulfonamidation reaction of 1H-1,2,3-triazole 1 with benzenesulfonyl chloride 2 in dichloromethane using a slight excess of triethylamine at 20 °C for 3 h. This procedure is distinguished by its short reaction time, high yield, excellent regioselectivity, clean reaction profile, and operational simplicity. The sulfonamide 3 was characterized by high-resolution mass spectrometry, FT–IR, UV–Vis, 1D and 2D NMR spectroscopy, and elemental analysis. The sulfonamide 3 exhibited moderate activity against UO-31 renal, SNB-75 central nervous system, HCT-116 colon, and BT-549 breast cancer cell lines, with growth inhibition percentages (GI%) ranging from 10.83% to 17.64%. [ABSTRACT FROM AUTHOR]
- Published
- 2022
- Full Text
- View/download PDF
46. Synthesis of Indolyl‐1,3‐dienes from β‐Sulphonyl Aldehydes through One‐Pot Sequential Brønsted Acid/Base Catalysis.
- Author
-
Karan, Ganesh, Sahu, Samrat, and Sudan Maji, Modhu
- Subjects
- *
BRONSTED acids , *SULFONYL group , *ALDEHYDES , *CATALYSIS , *DIELS-Alder reaction , *SCHIFF bases , *SULFONYL compounds - Abstract
Introduction of a 1,3‐diene moiety at the C3‐position of pyrrole and indole bearing various aliphatic as well as aromatic functional groups with good stereoselectivity remains a challenging task. Keeping the synthetic applicability in mind, an eccentric strategy is developed to synthesize 1,3‐dienyl pyrroles and indoles from unprotected pyrroles and indoles employing β‐sulphonyl aldehyde as a dienylating agent. This method is developed by using a one‐pot sequential Brønsted acid/base catalysis strategy. The nucleophilicity of indole is transmitted through the conjugation to eliminate the sulfonyl groups in a step‐wise manner. Further, this developed protocol was extended to the incorporation of a 1,3,5‐triene moiety at the C3‐position of indoles through unprecedented successive three sulfonyl group elimination. As an application of this strategy, a Diels−Alder reaction and hydrothiolation of 1,3‐diene were demonstrated. [ABSTRACT FROM AUTHOR]
- Published
- 2022
- Full Text
- View/download PDF
47. Water‐Promoted Michael Addition Reaction of Sulfonyl Hydrazides and α, β‐Unsaturated Propionic Acids to 3‐Sulfone Propionic Acids.
- Author
-
Qi, Zhiyuan, Liu, Yifan, Zhang, Qilong, Zhao, Panfeng, Gao, Lingfeng, Sun, Xu, and Zheng, Gengxiu
- Subjects
- *
MICHAEL reaction , *PROPIONIC acid , *SULFONYL compounds , *HYDRAZIDES , *SULFONES , *CATALYSTS , *COLUMN chromatography , *ORGANIC solvents - Abstract
A water‐promoted synthesis methodology for constructing 3‐sulfone propionic acids from sulfonyl hydrazides and α, β‐unsaturated propionic acids with excellent yields were reported. The green synthesis methodology was promoted by water without any catalyst, ligand and organic solvent. The D2O control experiment sufficiently proved that the 2‐hydrogen atom of 3‐sulfone propionic acid come from water. Moreover, the 3‐sulfone propionic acid derivates could be directly purified by crystallization without column chromatography. [ABSTRACT FROM AUTHOR]
- Published
- 2022
- Full Text
- View/download PDF
48. Synthesis of Benzimidazole-Sulfonyl Derivatives and Their Biological Activities.
- Author
-
Mulugeta, Endale and Samuel, Yoseph
- Subjects
- *
CARBONIC anhydrase , *SULFONYL compounds , *BENZIMIDAZOLES - Abstract
Currently, the synthesis of new compounds with potential bioactivities has become a central issue in the drug discovery arena. Among these new compounds, benzimidazole-sulfonyl scaffolds have vital applications in the fields of pharmaceuticals industries. Benzimidazole and sulfonyl compounds have remarkable biological activities, such as antibacterial, antifungal, anti-inflammatory, antiproliferative, carbonic anhydrase inhibitory, and α-amylase inhibitory activities. Furthermore, recent literature mentions the synthesis and bioactivities of some benzimidazole-sulfonyl hybrids. In this review, we focus on reviewing the synthesis of these hybrid scaffolds and their various types of biological activities of the compounds. [ABSTRACT FROM AUTHOR]
- Published
- 2022
- Full Text
- View/download PDF
49. Sulfonyl hydrazide induced sulfenylation of imidazoheteroarenes: A 'catalyst and solvent free' protocol.
- Author
-
Mal, Sourav and Jana, Manoranjan
- Subjects
- *
CATALYSTS , *SUSTAINABLE chemistry , *HYDRAZIDES , *SULFONYL compounds , *BIOCHEMICAL substrates - Abstract
A simple and hassle free sustainable protocol for the sulfenylation of imidazoheterocycles has been developed. Sulfonyl hydrazides have been used as the generator of active thio carrier in situ in the form of "sulfono thionate" under neat condition to produce the desired sulfenylated imidazoheterocycles in good to excellent yields. The new methodology does not demand the requirement of any solvent or catalyst by simply regulating the proportion of reactants. Thus, the methodology is greener and easy to handle. [ABSTRACT FROM AUTHOR]
- Published
- 2022
- Full Text
- View/download PDF
50. Effect of cysteine thiols on the catalytic and anticancer activity of Ru(II) sulfonyl-ethylenediamine complexes.
- Author
-
Chen, Feng, Romero-Canelón, Isolda, Habtemariam, Abraha, Song, Ji-Inn, Banerjee, Samya, Clarkson, Guy J., Song, Lijiang, Prokes, Ivan, and Sadler, Peter J.
- Subjects
- *
NAD (Coenzyme) , *ANTINEOPLASTIC agents , *CATALYTIC activity , *RUTHENIUM catalysts , *THIOLS , *TRANSFER hydrogenation , *X-ray crystallography , *SULFONYL compounds - Abstract
We have synthesized a series of novel substituted sulfonyl ethylenediamine (en) RuII arene complexes 1–8 of [(η6-arene)Ru(R1-SO2-EnBz)X], where the arene is benzene, HO(CH2)2O-phenyl or biphenyl (biph), X = Cl or I, and R1 is phenyl, 4-Me-phenyl, 4-NO2-phenyl or dansyl. The 'piano-stool' structure of complex 3, [(η6-biph)Ru(4-Me-phenyl-SO2-EnBz)I], was confirmed by X-ray crystallography. The values of their aqua adducts were determined to be high (9.1 to 9.7). Complexes 1–8 have antiproliferative activity against human A2780 ovarian, and A549 lung cancer cells with IC50 values ranging from 4.1 to >50 μM, although, remarkably, complex 7 [(η6-biph)Ru(phenyl-SO2-EnBz)Cl] was inactive towards A2780 cells, but as potent as the clinical drug cisplatin towards A549 cells. All these complexes also showed catalytic activity in transfer hydrogenation (TH) of NAD+ to NADH with sodium formate as hydride donor, with TOFs in the range of 2.5–9.7 h−1. The complexes reacted rapidly with the thiols glutathione (GSH) and N-acetyl- L -cysteine (NAC), forming dinuclear bridged complexes [(η6-biph)2Ru2(GS)3]2− or [(η6-biph)2Ru2(NAC-H)3]2−, with the liberation of the diamine ligand which was detected by LC-MS. In addition, the switching on of fluorescence for complex 8 in aqueous solution confirmed release of the chelated DsEnBz ligand in reactions with these thiols. Reactions with GSH hampered the catalytic TH of NAD+ to NADH due to the decomposition of the complexes. Co-administration to cells of complex 2 [(η6-biph)Ru(4-Me-phenyl-SO2-EnBz)Cl] with L -buthionine sulfoximine (L -BSO), an inhibitor of GSH synthesis, partially restored the anticancer activity towards A2780 ovarian cancer cells. Complex 2 caused a concentration-dependent G1 phase cell cycle arrest, and induced a significant level of reactive oxygen species (ROS) in A2780 human ovarian cancer cells. The amount of induced ROS decreased with increase in GSH concentration, perhaps due to the formation of the dinuclear Ru-SG complex. [ABSTRACT FROM AUTHOR]
- Published
- 2022
- Full Text
- View/download PDF
Catalog
Discovery Service for Jio Institute Digital Library
For full access to our library's resources, please sign in.