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A facile synthetic strategy is reported to afford bioactive quinazolinones and aromatic amines by employing amorphous cobalt hollow nanospheres (Co HNS) derived from a Bio‐MOF, cobalt adeninate, as a catalyst. Modulated electron states of the amorphous cobalt with a high concentration of surficial active sites and Co–N sites enhance the intrinsic catalytic activity while the support, activated carbon, facilitates the formation of hollow structure. [ABSTRACT FROM AUTHOR]

An efficient and one‐step synthesis of quinazolinones using 2‐aminobenzamide and benzylamine in DMSO under external catalyst‐ and base‐free conditions is reported. A broad substrate scope and environment‐benign mild reaction conditions are the major attributes of this straightforward synthesis. Moreover, the synthesized quinazolinone derivatives were used to produce pharmaceutically active rutaecarpine analogues using a two‐step reaction: N‐alkylation followed by intramolecular cyclization. [ABSTRACT FROM AUTHOR]

Quinazolinone‐coumarin conjugates synthesized through Late‐Stage Functionalization approach are evaluated for their in vitro biological activity for 60 human cancer cell lines representing nine different cancer types. Among the synthesized compounds, eight displayed significant growth inhibitory activity across a spectrum of cancer types, with compound 23 demonstrating particularly notable cytotoxicity. Further investigation involved a five‐dose assay of compound 23 against NCI‐60 cancer cell lines, revealing its efficacy at different concentrations. Additionally, binding studies elucidated its interaction with Human Serum Albumin (HSA) and DNA. The results indicated a strong binding affinity of 23 with HSA, evidenced by a high binding constant (2.26 × 105 M−1). Moreover, its interaction with DNA occurred via intercalation, specifically between the base pairs of DNA strands, with a binding constant of 5.51 × 104 M−1. This suggests that compound 23 has the ability to bind to both DNA and transport proteins, making it a promising pharmacophore with potential therapeutic applications. [ABSTRACT FROM AUTHOR]

Quinazolinone and thiouracil derivatives are key scaffolds in anticancer development. This study used a molecular hybridization approach to synthesize new quinazolinone‐thiouracil derivatives and evaluated their anticancer activity against three human cancer cell lines, namely breast, lung, and glioblastoma, using SRB assay. Structural elucidation was performed using IR spectroscopy, 1H‐NMR, 13C‐NMR, mass spectrometry, and elemental analysis. Most compounds show moderate to significant cytotoxic effects, with compound 5d displaying the highest potency (IC50 values of 5.28, 4.02, and 2.88 µM, respectively). Compound 5d also demonstrated comparable potency to positive controls cisplatin and temozolomide in lung and glioblastoma cancer cell lines and was nearly as effective as mitochondrial division inhibitor‐1 (mdivi‐1). Furthermore, molecular docking analyses revealed strong binding interactions of the synthesized compounds with dynamin‐related protein‐1 (drp1). Protein–ligand stability studies and all‐atom simulation confirmed the stable binding of compound 5d with drp1. In conclusion, this study identified compound 5d as a potent drp1 inhibitor and promising anticancer drug candidate, deserving further investigation. [ABSTRACT FROM AUTHOR]

Novel 1,2,3‐triazole acetamide linked quinazolinone derivatives were synthesized via click reaction, by reacting of 3‐methyl‐2‐(prop‐2‐yn‐1‐ylthio)quinazolin‐4(3H)‐one with various aryl azides as prominent fungal pathogen Candida albicans interactions. The prepared triazole compounds were characterized using mass spectrometry, 1H NMR, 13C NMR, and IR spectroscopic techniques. Compounds were screened for their in vitro antibacterial and antifungal activity against a variety of microorganisms namely, Bacillus subtilis, Enterococcus faecalis, Klebsiella pneumonia, Escherichia coli, Aspergillus fumigatus, Candida albicans, and Aspergillus clavatus. Quinazolinone linked p‐hydroxyphenyl, o, p‐dihydroxyphenyl and o‐dimethylamino phenyl triazoles showed a remarkable antibacterial activity against E. faecalis with MIC values of 3.20±0.01, 4.01±0.04, and 4.10±0.01 μg mL−1, and screened compounds p‐nitrophenyl substituted triazole, and p‐methylphenyl substituted triazole displayed a significant antifungal activity against C. albicans with MICs of 3.16±0.01, 4.06±0.03 μg mL−1, compared to itraconazole (MIC=3.32±0.02 μg mL−1). For further exploration of the anti‐fungal mechanism of action, molecular docking was carried out for these compounds in C. albicans active site as one of the important antifungal inhibitors (PDB: 1A19). Furthermore, the ADMET profile was evaluated for all the final triazole compounds in contrast to reference drugs moxifloxacin and itraconazole. In conclusion, we discovered a novel quinazolinone linked 1,2,3‐triazoles with promising antimicrobial activity and a favorable pharmacokinetic profile. [ABSTRACT FROM AUTHOR]

Copper‐catalyzed and visible‐light catalytic difluoroalkylation reactions of N‐cyanamide alkenes have been developed. Various α‐bromodifluoromethyl substituted esters, amides and heterocycles were employed as the CF2 source. Both protocols are characterized by medium to high yields, good functional group compatibility, and applicable to gram‐scale synthesis. Comparable studies of copper catalysis and photoredox catalysis demonstrate minimal differences between the two protocols. Preliminary mechanism suggest that both transformations involve tandem radical cyclization process. [ABSTRACT FROM AUTHOR]

We described a base‐promoted O‐arylation of N3‐hydroxyl quinazolinones with diaryliodonium salts and sequential BF3 ⋅ OEt2 and visible light‐controlled [3,3]‐ or [1,3]‐rearrangements of quinazolinone N−O aryl moieties to prepare a variety of 2‐(quinazolin‐4‐yloxy)phenols and atropisomeric 3‐(2‐hydroxyphenyl)quinazolin‐4‐ones in 44%‐75% yields and 28%‐70% yields, respectively. Mechanistic studies showed that HBF4 generated in situ from BF3 ⋅ Et2O and water served as the catalyst in this process and aryloxyquinazolinium salts are vital intermediates promoting the [3,3]‐ or [1,3]‐rearrangements. The N−O aryl moieties of aryloxyquinazolinium salts were found to undergo solely [3,3]‐rearrangement with heating whereas [1,3]‐rearrangement occurred via a radical process under irradiation of visible light. This method highlights the formation of aryloxyquinazolinium salts based on the use of BF3 ⋅ OEt2 and visible light to prompt [1,3]‐rearrangement generating atropisomeric quinazolinones. [ABSTRACT FROM AUTHOR]

Herein, we reported a selective, mild method for the visible‐light‐photocatalyzed trifluoromethylation and cyclization of unactivated tethered alkenes to provide tri‐ and tetracyclic quinazolinones. Trifluoroacetic acid and anhydride are inexpensive and readily available reagents for the process that proceeds without the addition of a strong oxidant. The wide substrate scope and the formation of 5‐ and 6‐membered rings are demonstrated in 44–82 % yields. Control experiments provide the basis for a proposed mechanism involving photocatalyzed SET from fac‐Ir(ppy)3 to TFAA and trifluoromethyl radical‐mediated regioselective cyclization. The practicality of the protocol was illustrated by a gram‐scale synthesis in 76 % yield. [ABSTRACT FROM AUTHOR]

A facile intramolecular [1,5] hydride transfer reaction in a Dihydroquinazolin‐4(1H)‐one moiety synthesized from anthranilamide, glutaraldehyde, and aromatic amines is described in isopropanol medium in the presence of catalytic HCl. Based on that, we have designed a simple, efficient strategy for conjugating quinazolinone, a pharmaceutically active moiety, with an aromatic amine through an aliphatic spacer. The use of isopropanol as a reaction medium at RT and isolation of the product without rigorous column purification make the process a step ahead towards sustainability. One of the synthesized compounds was evaluated as a small molecule DNA binder. Detailed binding properties were investigated by the multispectroscopy methods. [ABSTRACT FROM AUTHOR]

This paper presents a amidinyl transfer reagent for the synthesis of nitrogen‐containing compounds, wherein N,N‐dimethylformamide is used as the C1 source to react with hexamethyldisilazane, generating the N,N‐dimethylformimidamide intermediate. This intermediate is then reacted with amines to induce amidinyl transfer. This protocol can be applied for the synthesis of N‐formamide, benzimidazole and quinazolinone, for which amine derivatives used as substrates under optimized conditions. The advantages of this method are its operational simplicity, high efficiency, structural diversity in products with favorable yields, and applicability in gram‐scale operations. [ABSTRACT FROM AUTHOR]

An efficient palladium‐catalyzed annulation of 3‐arylquinazolinones with mono and double alkyne insertion was developed for the synthesis of fused quinazolinone derivatives in 43–80 % yields. A notable effect was observed in product yield, when bases/additives were modulated. The reaction mechanism is believed to proceed through C−X cleavage/alkyne insertion/1,4‐Pd migration and C−H annulation in a one‐pot manner. [ABSTRACT FROM AUTHOR]

Facile synthesis for true intermediate (E)‐ and Z‐2‐(((5‐bromo‐1‐(3‐chloropyridin‐2‐yl)‐1H‐pyrazol‐3‐yl)methylene)amino)‐5‐chloro‐3‐methylbenzoic acid precursors and 2‐(5‐bromo‐1‐(3‐chloropyridin‐2‐yl)‐1H‐pyrazol‐3‐yl)‐6‐chloro‐3,8‐dimethylquinazolin‐4(3H)‐one (QPP) as electron donor/electron acceptor to be working as efficient dye sensitizers. These new derivatives have a wide‐band gap photo‐catalysts semiconductor and are performing to spread to the visible‐light region to give more stability and efficiency towards biomedicine for different diseases. In the present work, the authors are suggesting the design and synthesis of new structures of QPP molecule with extended visible light absorptivity due to the extended π‐π/n‐π conjugations, to stimulate TiO2 nanoparticles in visible‐light region. The physicochemical characterizations confirmed the successful synthesis of QPP, TiO2, and QPP II/TiO2 samples with the proposed structures. Fixing of QPP on the TiO2 surface is refining the optical properties of TiO2 with enhancing the charge separation and generating the efficient antenna in the visible region. Furthermore, the QPP II/TiO2 sample achieved a threefold enhancement in the observed rate constant of the photo‐degradation of rhodamine B dye when compared to the bare TiO2. Finally, the effect of the scavengers was investigated by O2.− to be the most reactive species, and the mechanism of the enhancement was suggested for investigation of the proposed structures in various photo‐catalytic and biomedical applications. [ABSTRACT FROM AUTHOR]

A three‐step synthesis of anti‐amoebic, ring‐fused mackinazolinones has been developed. A Mannich‐type reaction between quinazolin‐4‐ones and N‐Cbz propanal in the presence of AgOTf afforded quinazolinones (19–94% isolated yield) bearing a newly formed heterocycle with an alkylamine appendage that, upon N‐Cbz deprotection and basification, triggered a domino rearrangement to afford 45 separable, ring‐fused products. Several compounds inhibited growth of Naegleria fowleri parasites that can cause a lethal human brain infection. Thus, the methodology provides immediate access to a promising anti‐amoebic scaffold. [ABSTRACT FROM AUTHOR]

A short and expeditious total and diverted total synthesis of luotonin, vasicinone, and their analogues has been achieved from the key tricyclic quinazolinone intermediate which was accessed from simple substituted anthranilamide obtained from the coupling of β‐alanate with isatoic anhydride followed by Dieckmann condensation chemistry of the resulting diester. The tricyclic ketone exhibited interesting chemical properties, e. g. keto‐enol tautomerism. Friedlander condensation and Fischer‐Indolization were employed for further annulations to access polycyclic alkaloids and their analogues. [ABSTRACT FROM AUTHOR]

We report catalytic hydroboration of esters as well as nitriles under solvent‐free and mild conditions using single titanium(IV) metal complex, [{κ2‐C6H4C(O)N(iPr)C(N‐iPr)=N}{κ3‐(iPr)N=C(O)−C6H4−NC(NMe2)N(iPr)}TiNMe2] 1 as a sustainable, economical, and efficient pre‐catalyst. The molecular structure of the TiIV complex in the solid state reveals the unique coordination of TiIV metal with N, N, and O atoms of one quinazolinone unit via in‐situ rearrangement, while another quinazolinone moiety coordinates in bidentate fashion via both N atoms only. The TiIV complex demonstrates excellent activity as a pre‐catalyst towards the hydroboration of a wide array of esters and nitriles with pinacolborane (HBpin) to afford alkoxyboranes and diboryl amines in high yield (up to 99 %) with greater tolerance to a variety of electron‐withdrawing and electron‐donating functional groups. A most plausible mechanism of hydroboration of esters is also proposed based on kinetics and NMR studies, which suggests the formation of titanium‐hydride species as an active catalyst. [ABSTRACT FROM AUTHOR]

Cyclopentadienyl manganese tricarbonyl (cymantrene) is known to undergo photochemical reactions by releasing one of its CO ligands. Here we present the first example of a photorearrangement of a cymantrenylmethyl fragment, where it retains all its three CO ligands. A tandem experimental and DFT (density functional theory)-based computational investigation allows us to explain this unexpected behavior: the rearrangement, indeed, begins with the release of one CO ligand, but cage effect of the solvent captures this CO molecule, allowing it to rapidly reattach once the rearrangement takes place. [ABSTRACT FROM AUTHOR]

Rhodium(III)‐catalyzed sp2/sp3 C−H activation/annulation of 2‐arylquinazolin‐4(3H)‐ones with 3‐methylmaleimides is explored. This protocol provides diversely functionalized isoindoloquinazolinones in good yields upon reaction with various maleimides. This Rh(III)‐catalyzed protocol can be applied for the chemo‐ and diastereoselective synthesis of various polyheterocycles. [ABSTRACT FROM AUTHOR]

In a previous report, we have already synthesized dinitro and dibromo derivatives of 2,2‐disubstituted‐quinazolin‐4(1H)‐one by a facile method. In order to give insight to our experimental results, we herein report on the theoretical investigations of reactivity of synthesized quinazolinone toward bromination and nitration by using density functional theory (DFT) calculations. The optimized molecular geometries of these compounds by using the B3LYP/6–31G(d, p) method have been compared with their X‐ray structures, which are in good agreement. The correlation between the experimental and computational geometrical data is above 90% and root mean square deviation (RMSD) is low ranging from 0.04% to 0.9% except N1‐H1 and N2‐H2 bond where RMSD goes to 1% due to hydrogen bonding between N1‐H1 .....O1 = C1 and N2‐H2 ....O1 = C1. The Mullikan charge distributions at the different atomic sites have been computed and nucleophilic site are guessed by molecular electrostatic potential (MEP) map. In addition, frontier molecular orbitals of these compounds were discussed at the same level of theory, confirming the nucleophilic sites at position 6 and 8 of 4‐quinazolinone. [ABSTRACT FROM AUTHOR]

This work synthesized a novel colorimetric ligand based on the compound quinazolinone (Sensor) and investigated it. The sensing activity of the sensor toward different cation was studied. The sensor demonstrated a highly selective colorimetric sensing toward Hg2+ with a detection limit of 0.1 ppb and visual color change from colorless to Purple in methanol‐water solvents (v/v, 10,90). The cation binding character was determined using visual inspection, UV–Vis, and fluorescence analyses. In the computational part, the interaction between the receptor and Hg2+ ion was investigated using density functional theory (TD‐DFT) and quantum theory of atoms in molecules (QTAIM) in the solution phase (in the presence of water as solvent and the CPCM model). Theoretical studies have shown that electronic properties such as energy gap, absorption energy, charge/energy transfer, and optical properties change dramatically in the presence of Hg2+ cations. Also, the effect of the electric field on the electronic properties of the sensor/Hg2+ complex improved the Hg2+ cation adsorption process. [ABSTRACT FROM AUTHOR]

In this research project, silica‐modified ZnFe2O4 magnetic nanoparticles were prepared in a simple, short, and straightforward way. Subsequently, an efficient catalyst through immobilization of ascorbic acid on the surface of silica‐coated ZnFe2O4 nanoparticles has been produced. The physical and chemical properties of ZnFe2O4@SiO2‐ascorbic acid were considered by X‐ray diffraction (XRD), Fourier transform infrared spectroscopy (FT‐IR), thermogravimetric analysis (TGA), scanning electron microscopy (SEM), Energy‐dispersive X‐ray spectroscopy (EDS), and vibrating sample magnetometer (VSM) analyses. The catalytic activity of described magnetic nanocatalyst was checked out for the synthesis of chromeno[2,3‐d] pyrimidine‐8‐amine and quinazolinone derivatives. The described catalyst was recovered and reused for five continuous cycles without considerable change in its catalytic activity. [ABSTRACT FROM AUTHOR]

The indolizines nucleus is an important element of many synthetic molecules with significant biological activity. An efficient methodology for the synthesis of a variety of indolizines from quinazolinone, pyridine, and chalcone via I2/FeCl3 has been described. The reaction was promoted through Zwitterion formation/cyclization/aromatization sequence, affording the desired products in moderate to very good yields. This approach is a highly efficient and convenient way to get derivatives of indolizines from readily accessible substrate under relatively mild reaction conditions. [ABSTRACT FROM AUTHOR]

Cancer is one of the leading causes of death. Globally a huge number of deaths and new incidences are reported annually. Heterocyclic compounds have been proved to be very effective in the treatment of different types of cancer. Among different heterocyclic scaffolds, quinazoline and quinazolinone core were found versatile and interesting with many biological activities. In the discovery of novel anticancer agents, the Quinazoline core is very effective. The FDA has approved more than 20 drugs as an anticancer bearing quinazoline or quinazolinone core in the last two decades. One prime example is Dacomitinib, which was newly approved for non‐small‐cell lung carcinoma treatment in 2018. These drugs work by different pathways to prevent the spread of cancer cell progression, including inhibition of different kinases, tubulin, kinesin spindle protein, and so forth. This review presented recent developments of quinazoline/quinazolinone scaffold bearing derivatives as anticancer agents acting as epidermal growth factor receptor (EGFR) vascular endothelial growth factor receptor (VEGFR), and dual EGFR/VEGFR inhibitors. [ABSTRACT FROM AUTHOR]

A novel, base‐ and ligand‐free one pot protocol for the synthesis of fused‐quinazolinone under microwave irradiation using environmentally friendly PEG‐400 as a solvent has been developed. Besides benzaldehyde, various benzyl alcohols and methyl arenes were used in this protocol, which extend its synthetic applicability. Photophysical study of this highly fluorescent framework was studied by fluorescent study. DFT and ESI/MS studies were carried out to justify the proposed mechanism. [ABSTRACT FROM AUTHOR]

A variety of pseudorutaecarpine derivatives were prepared in good to excellent yields through a gold(I)‐catalyzed selective cyclization and 1,2‐shift of N‐alkynyl quinazolinone‐tethered indoles. Mechanistic study revealed that spiroindolenines generated in situ by cyclization at the the indole C3 position underwent an alkenyl 1,2‐shift to generate pseudorutaecarpine. The reaction proceeds under mild reaction conditions, has a broad substrate scope, good functional group tolerance, and gram‐scalable application. Furthermore, biological evaluation showed that most of the pseudorutaecarpine scaffolds prepared exhibit anti‐inflammatory activity. [ABSTRACT FROM AUTHOR]

A mild, external photocatalyst‐ and additive‐free protocol for photo‐induced alkylation/cyclization of unactivated alkenes with halides has been developed. This strategy showed excellent regioselectivity and simple operation to synthesize alkyl‐substituted quinazolinones with a broad substrate scope. More importantly, chlorinated alkanes were also compatible with this transformation. [ABSTRACT FROM AUTHOR]

Tunable C−H activation cascade reactions between quinazolinones and cyclopropenones have been developed. Notably, cyclopropenones, acting as multi‐functional building blocks, could be assembled to construct up to 10 distinct heterocyclic scaffolds in a one‐pot manner. [ABSTRACT FROM AUTHOR]

A transition‐metal‐catalyzed C−H activation cascade strategy to rapidly construct diverse quinazolinone derivatives in a one‐pot manner is reported. The catalysts play an important role in the different transformations. Additionally, the procedure is scalable, proceeds with high efficiency and good chemo‐/regio‐selectivity, and tolerates a range of functional groups. [ABSTRACT FROM AUTHOR]

Chiral 2‐alkylquinazolinones are key synthetic intermediates, but their preparation in high optical purity is challenging. Thus, a multicomponent procedure integrating anthranilic acids, N‐Boc‐amino acids, and amines in the presence of methanesulfonyl chloride, N‐methylimidazole, and copper(II) chloride was developed to mildly afford N‐Boc‐2‐alkylaminoquinazolin‐4(3H)‐ones with excellent preservation of enantiomeric purity (>99% ee). Copper(II) chloride was essential to retaining enantiopurity, and reaction component structural changes were well tolerated, resulting in an efficient, all‐in‐one procedure that promotes sequential coupling, lactonization, aminolysis, and cyclization in good yields. The method was applied to the rapid assembly of four key intermediates used in the synthesis of high profile quinazolinones, including several PI3K inhibitor drugs. [ABSTRACT FROM AUTHOR]

A facile and general transition‐metal‐free access to 1‐substituted‐4‐quinazolinones 2 has been achieved based on the proline‐mediated cyclization of carbamoylbenzamides 1 in the presence of potassium t‐butoxides in DMSO at 100 °C within several hours. The gram‐scale synthesis of 1‐phenyl‐4‐quinazolinone 2 a has also been achieved without the loss of efficiency. The one‐pot synthesis of 1‐phenyl‐4‐quinazolinone 2 a has proven to be possible starting from 2‐bromobenzamide and phenylisocyanate in an acceptable yield. The present reactions were assumed to proceed through radical intermediates as the major path and also the SNAr route as a minor path based on several control experiments. [ABSTRACT FROM AUTHOR]

Currently available drugs being used to treat leishmaniasis have several shortcomings, including high toxicity, drug administration that requires hospitalization, and the emergence of parasite resistance against clinically used drugs. As a result, there is a dire need for the development of new antileishmanial drugs that are safe, affordable, and efficient. In this study, two new series of synthesized quinazolinone derivatives were investigated as potential future antileishmanial agents, by assessing their activities against the Leishmania (L.) donovani and L. major species. The cytotoxicity profiles of these derivatives were assessed in vitro on Vero cells. The compounds were found to be safer and without any toxic activities against mammalian cells, compared to the reference drug, halofuginone, a clinical derivative of febrifugine. However, they had demonstrated poor antileishmanial growth inhibition efficacies. The two compounds that had been found the most active were the mono quinazolinone 2d and the bisquinazolinone 5b with growth inhibitory efficacies of 35% and 29% for the L. major and L. donovani 9515 promastigotes, respectively. These outcomes had suggested structural redesign, inter alia the inclusion of polar groups on the quinazolinone ring, to potentially generate novel quinazolinone derivatives, endowed with effective antileishmanial potential. [ABSTRACT FROM AUTHOR]

Pd‐catalyzed decarboxylative ortho‐aroylation of 2‐aryl‐quinazolinones with α‐oxocarboxylic acids for the synthesis of diaryl ketones has been developed. Biologically interested novel quinazolinones with diaryl ketone functionality has been obtained with moderate to excellent yield from easily accessible 2‐aryl‐quinazolinones having inherent directing group. [ABSTRACT FROM AUTHOR]

In this study, quinazolinone derivatives have been synthesized via a suitable and efficient procedure by one‐potmulti‐component reactions of 3‐amino‐1,2,4‐triazole or 2‐aminobenzimidazole, dimedone and aromatic aldehydes in the presence of Fe3O4@TiO2‐IL as nanocatalyst under solvent‐free condition. The products were prepared in good to excellent yields using Fe3O4@TiO2‐IL magnetic nanocatalyst. The Fe3O4@TiO2 magnetic nanoparticles (MNPs) were prepared using beet juice extract and functionalized with IL based on DABCO. Moreover, the core‐shell structured magnetic Fe3O4@TiO2‐IL has been characterized by different techniques such as 1H‐NMR, FT‐IR, VSM, XRD, SEM, TGA, TEM and EDX. To the best of our knowledge, the prepared ionic liquid displayed a good protective and activator agent for magnetic nanocatalyst. [ABSTRACT FROM AUTHOR]

In this research, a novel strategy for synthesis of quinazolinones has been formulated via one pot condensation of aromatic aldehydes, isatoic anhydride, and aniline by employing prepared povidone‐phosphotungstic acid (PVP‐PWA) hybrid as a novel solid acid heterogenous catalyst in methanol at 80 °C. The synthesized PVP‐PWA is confirmed by FTIR, XRD and studied for TGA, BET plots. The reaction is optimized for different solvents and loading of catalyst. The yields of all quinazolinone derivatives are observed in the range of 78–86%. All the synthesized quinazolinones are investigated by spectral data. The use of ecologically benign catalyst, good atom economy, environmental affordability, and easy work up makes this protocol sustainable. [ABSTRACT FROM AUTHOR]

An efficient and rapid one‐pot synthesis of quinazolinone via a three‐component carbonylative coupling of 2‐aminobenzamide or 2‐aminobenzonitrile, Mo(CO)6 and aryl bromides has been developed recently. This method provide a new way to synthesize quinazolinone which has a wide substrate scope, good functional group tolerance and mild reaction condition. [ABSTRACT FROM AUTHOR]

Summary of main observation and conclusion: A facile approach to chiral dihydroquinazolinone derivatives has been described via biomimetic asymmetric reduction of quinazolinones with chiral and regenerable NAD(P)H models. The utility of this method was demonstrated by a concise synthesis of the bromodomain protein divalent inhibitor. [ABSTRACT FROM AUTHOR]

Supporting information for this article is given via a link at the end of the document. By intercepting the acylpalladium species with C=N bond of azaarenes or imines other than free amines or alcohols, the difunctionalization of C=N bond was established via palladium‐catalyzed carbonylation/nucleophilic addition sequence. This method is compatible with a diverse range of azaarenes and imines and allows for the efficient synthesis of a wide range of quinazolinones and derivatives. The synthetic utility has been demonstrated by one‐step synthesis of evodiamine and its analogue with inexpensive starting materials. [ABSTRACT FROM AUTHOR]

A highly efficient 2‐chloroquinazolin‐4(3H)‐one rearrangement was developed that predictably generates either twisted‐cyclic or ring‐fused guanidines in a single operation, depending on the presence of a primary versus secondary amine in the accompanying diamine reagent. Exclusive formation of twisted‐cyclic guanidines results from pairing 2‐chloroquinazolinones with secondary diamines. Use of primary amine‐containing diamines permits a domino quinazolinone rearrangement/intramolecular cyclization, gated through (E)‐twisted‐cyclic guanidines, to afford ring‐fused N‐acylguanidines. This scalable, structurally tolerant transformation generated 55 guanidines and delivered twisted‐cyclic guanidines with robust plasma stability and an abbreviated total synthesis of an antitumor ring‐fused guanidine (4 steps, 55 % yield). [ABSTRACT FROM AUTHOR]

Heterocyclic compounds with different heterocycle moieties, namely benzoxazinone, benzimidazole, quinazolinone, and benzofuranone heterocyclic rings, were synthesized, characterized and evaluated for their anticancer activities against Lung cancer cell line (A549) using Sulforhodamine B (SRB) assay. In vitro, a compound with benzoxazinone scaffold namely 2‐benzyl‐3,1‐benzoxazin‐4‐one was shown to have the best antiproliferative activity against Lung cancer cell line (A549) with IC50 values 53.9 μM in comparison with other heterocyclic rings. This compound showed an excellent cytotoxicity effect against the pancreatic cancer cell line (PANC‐1) with IC50 values 0.15 μM, while it has a slight effect on the hepatocellular carcinoma cell line (HepG2). [ABSTRACT FROM AUTHOR]

The possibility of a single‐stage solvent‐free stereoselective synthesis of a spirocyclic compound from the natural bicyclic monoterpenoid (−)‐fenchone and anthranilamide has been shown for the first time. The molecular and crystal structure of (1R,2S,4S)‐1,3,3‐trimethyl‐1′H‐spiro[bicyclo[2.2.1]heptane‐2,2′‐quinazolin]‐4′(3′H)‐one, C17H22N2O, was established by X‐ray diffraction though the chirality was assumed via the known reactant connectivity and 1H and 13C NMR spectroscopy. It has shown that in the molecule, for steric reasons, there is an elongation of the Me2C—C(N)N bond to 1.603 (5) Å. The formation of dimers via N—H...O=C hydrogen bonds with an interaction energy of 93.30 kJ mol−1 and through cavities (33.7% of the unit‐cell volume) was established in the packing of the molecules. There are no π‐stacking interactions in the structure. [ABSTRACT FROM AUTHOR]

A visible‐light‐enabled selective oxidation of alcohols to aldehydes has been developed under transition‐metal‐free conditions. Utilizing eosin Y as the direct hydrogen‐atom transfer (HAT) photocatalyst and molecular oxygen as the terminal oxidant, both aromatic and aliphatic aldehydes could be obtained in moderate to good yields. Using this approach, various quinazolinones, including two real drug molecules, were easily synthesized from the corresponding o‐aminobenzamides and alcohols. [ABSTRACT FROM AUTHOR]

Here we report graphene oxide (GO) promoted 3‐component reaction of isatoic anhydride, benzylamines and dimethyl sulfoxide (DMSO) as one carbon source. Synthesized GO was well characterized by SEM, XRD, EDX, XPS and thermal stability was confirmed by TGA. A series of 3‐substituted quinazolinone was developed under mild and environmentally friendly conditions in moderate to good yields. A tentative mechanism is also proposed. We have developed an efficient, environmentally benign new method of synthesis of 3‐substituted quinazolinones from isatoic anhydride, benzylamines and dimethyl sulfoxide (DMSO) as one carbon source, using Graphene oxide (GO) as recyclable green reaction promoter. [ABSTRACT FROM AUTHOR]

In this paper, a novel method is introduced for the synthesis of 3‐substituted 2‐thioxo‐2,3‐dihydroquinazolin‐4(1H)‐one derivatives. This methodology is based on the multicomponent one‐pot reaction of isatoic anhydride, amines, chloroform and sulfur in basic conditions. The products are obtained in highest efficiency when the reaction is performed in 1,4‐dioxane as the solvent in the presence of potassium tert‐butoxide as the base. The reaction showes to be efficient and simple for the preparation of these compounds. In addition, this method is general and different aromatic or aliphatic amines are used and the desired products are isolated in high yields. A possible mechanism for the reaction is proposed, which consisted the dichlorocarbene formation under the basic conditions. In this paper, a novel method is introduced for the synthesis of 3‐substituted 2‐thioxo‐2,3‐dihydroquinazolin‐4(1H)‐one derivatives, based on the multicomponent one‐pot reaction of isatoic anhydride, amines, chloroform and sulfur in basic conditions. The optimal reaction condition is 1,4‐dioxane solvent in the presence of potassium tert‐butoxide base. This is a general method and different aromatic or aliphatic amines can successfully be used. A possible mechanism for the reaction is suggested, which consists in the dichlorocarbene formation under basic conditions. [ABSTRACT FROM AUTHOR]

Abstract: An efficient and convenient copper‐mediated tandem C(sp2)‐H amination and annulation of arenes with 2‐aminopyridines to provide 11H‐pyrido[2,1‐b]quinazolin‐11‐ones has been developed. A variety of benzamides and 2‐aminopyridines bearing different substituents are compatible with this transformation [ABSTRACT FROM AUTHOR]

Nanomagnetic SrFe12O19 was synthesized through a simple sol–gel auto-combustion and then characterized by FT-IR, XRD, EDXA, VSM, BET and SEM image. Moreover, it was used as catalyst for the first time in the modified Niementowski reaction to investigate its catalytic activity. According to the high yield of quinazolinone products obtained within short reaction times, it was found that SrFe12O19 can be used as an effective and green nanocatalyst in organic reactions. The nanomagnetic catalyst can be easily separated from the reaction mixture using an external magnet. [ABSTRACT FROM AUTHOR]

Asymmetric arylation of 4-fluoroalkyl-2-quinazolinone derivatives with arylboronic acids proceeded smoothly in the presence of a cationic palladium catalyst (1 mol %) coordinated with a chiral phosphinooxazoline (phox) ligand to create the corresponding fluorine-containing arylated dihydroquinazolinones in high yields and with greater than 99 % ee. [ABSTRACT FROM AUTHOR]

Reactions of 6-bromo-2-isopropyl-4(3H)-3,1-benzoxazin-4-one toward mono- and di-dentate nitrogen nucleophiles, e.g. primary aliphatic and , 1,2-phenylenediamine, hydrazine hydrate, and formamide, have been investigated and afford the corresponding quinazolinones which are expected to have some interesting . The behavior of 3, 1-benzoxazin-4-one toward active methylene compounds, namely, acetylacetone in basic medium has been studied and gave 3-acetylquinoline. The last reaction is considered as an illustrative model of heterocyclic transformation reactions. [ABSTRACT FROM AUTHOR]

An efficient copper-catalyzed tandem aerobic oxidative annulation and carbon-carbon bond cleavage reaction was developed from easily accessible arylacetamides, which provides a direct approach for the domino synthesis of a vast array of tricyclic or tetracyclic fused quinazolinone alkaloid structures. A plausible reaction mechanism is proposed involving an aerobic benzylic oxidation/cyclization/decarbonylation cascade. [ABSTRACT FROM AUTHOR]