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A new series of 4-methyl-2-{2-[(aryl)methylidene]hydrazinyl}-1,3-thiazole (2a-i), N-(4-acetyl-5-aryl)4,5-dihydro-1,3,4-thiadiazol-2-yl)acetamides (3a-b) and N-(5-(4-(substituted phenyl)-1,3,4-thiadiazol-2-yl)acetamides (3c-i) were synthesized by the reaction of 2-((aryl)methylene)hydrazine-1-carbothioamides (1a-i) and acetic anhydride or chloroacetone. The cytotoxic activities of the products were evaluated by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay against Hela cervical cancer, MCF-7 breast carcinoma and HT-29 colorectal cancer cell lines. Thiazole based compounds 2a, 2b, 2f and 2i, bearing 4-bromothiophen-2-yl, naphthalen-2-yl, 2,5-difluorophenyl and 4-(trifluoromethoxy)phenyl moieties, respectively; also N-(4-acetyl-5-(naphthalen-2-yl)-4,5-dihydro-1,3,4-thiadiazol-2-yl)acetamide (3b) and N-(5-(2,6-difluorophenyl)-1,3,4-thiadiazol-2-yl)acetamide (3d) exhibited significant anticancer activity against three cancer cell lines. Moreover, these active compounds were further evaluated by apoptotic protein levels. The results showed that these thiazole and thiadiazole compounds induced apoptosis of cancer cells. [ABSTRACT FROM AUTHOR]

Novel 2-heteroaryl-N-[4-(substituted aryl)thiazol-2-yl]propanamide derivatives (7a–7o) were synthesized and investigated for their antimicrobial activity. Among the tested compounds, 2-[(1H-Benzimidazol-2-yl)thio]-N-[4-(naphthalen-2-yl)thiazol-2-yl]propanamide (7e) and N-[4-(4-Chlorophenyl)thiazol-2-yl]-2-[(1-methyl-1H-tetrazol-5-yl)thio]propanamide (7f) showed the highest antibacterial activity, whereas 2-[Benzothiazol-2-ylthio]-N-[4-(4-chlorophenyl)thiazol-2-yl]propanamide (7i) and 2-[(1H-Benzimidazol-2-yl)thio]-N-[4-(4-chlorophenyl)thiazol-2-yl]propanamide (7j) displayed anticandidal effect against C. parapsilosis and C. glabrata. The cytotoxic activity of the compounds (7a–7o) was also tested against HL-60 human leukemia cells, THP-1 human monocytic leukemia cells, and NIH/3T3 mouse embryonic fibroblast cells. Compound N-[4-(4-Chlorophenyl)thiazol-2-yl]-2-[(1-methyl-1H-imidazol-2-yl)thio]propanamide (7 g) and compound 7j exhibited high cytotoxicity against HL-60; and compounds 2-[(1-Methyl-1H-imidazol-2-yl)thio]-N-[4-(naphthalen-2-yl)thiazol-2-yl]propanamide (7b), 7 g and N-[4-(4-Methoxyphenyl)thiazol-2-yl]-2-[(4-methyl-4H-1,2,4-triazol-3-yl)thio]propanamide (7 m) also had cytotoxic activity against THP-1 compared with standard drug with selective profile. Additionally, in silico physicochemical properties of the compounds were described. [ABSTRACT FROM AUTHOR]

Nine new thiazole derivatives were synthesized considering 6-acetyl penicillanic acid (6-APA) and investigated for their antimicrobial activity. Ethyl 2-(2-mercaptoacetamido)-4-methylthiazole-5-carboxylate derivatives (3a–3i) were gained with a two-step synthetic method using conventional Hantzsch thiazole synthesis. The structural elucidation of the compounds was performed by 1H-NMR, 13C-NMR spectral data and HRMS. All compounds were tested on eleven bacteria and sixteen fungi species and minimum inhibitory concentration (MIC) was determined for each. Compounds 3d (4-methyl-2-(2-((5-methyl-1,3,4-thiadiazol-2-yl), 3f (4-methyl-2-(2-((5-nitro-1H-benzimidazol-2-yl) and 3g (4-methyl-2-(2-((5-methyl-4H-1,2,4-triazol-3-yl) bearing thiazole, 5-nitrobenzimidazole and triazole rings respectively exhibited high antimicrobial activity against most of the strains. In silico physicochemical properties were calculated for the compounds and it was detected that they comply with the rules of drug availability. [ABSTRACT FROM AUTHOR]

Thiazole, a five-membered heterocyclic compound constitutes the skeleton of various commercially marketed drug candidates and the heart-core in a diverse range of entities of biological and medicinal interest. It is a versatile and essential component of natural products and medicinally significant heterocyclic compounds. The chemistry of thiazoles was widely developed in terms of anti-microbial, anti-cancer, anti-tubercular, anti-oxidant, anti-inflammatory, and other therapeutically active agents after the pioneering work of Hofmann and Hantzsch, Bogert and coworkers in 1887. Besides these, thiazole heterocycles are also useful as the constituents of several dyes and photographic materials. The present review encompasses and highlights the recent progress in the development of thiazole based heterocyclic compounds for various applications focusing it a scaffold of biological and medicinal interest. [ABSTRACT FROM AUTHOR]

Newly synthesized 4-substituted phenyl-2-(4-substituted phenylpiperazine-1-yl)thiazole derivatives (4a–v) were evaluated in terms of their acetylcholinesterase (AChE) inhibition activities. Twenty-two compounds were tested against AChE at six different concentrations that varied between 10−4 and 10−9 M. The concentrations that inhibited AChE were calculated between 1.15 and 3.45 µM in seven compounds (4a, 4b, 4h, 4l, 4m, 4q, 4r). Compounds 4m, 4b, and 4l represented 1.15, 1.31, 1.34 µM (IC50) inhibitions, respectively. Although the inhibition values are lower than that of donepezil, they are considerable. Modeling studies of these analogs revealed similar positioning with donepezil, in which Ar–Ar interactions with Tyr337 and Trp 286 exist. [ABSTRACT FROM AUTHOR]

New N-(5-methyl-4-phenylthiazol-2-yl)-2-(substituted thio)acetamides were synthesized and studied for their anticancer activity. The title compounds were procured by reacting 2-chloro-N-(5-methyl-4-phenylthiazol-2-yl)acetamide with some mercapto derivatives. The structural elucidation of the compounds was performed by 1H-NMR, 13C-NMR and LC-MS/MS spectral data and elemental analyses. The synthesized compounds were investigated for their antitumor activities against A549 human lung adenocarcinoma cells and NIH/3T3 mouse embryoblast cell line for determining their selective cytotoxicity. 2-[(1-methyl-1H-tetrazol-5-yl)thio]-N-(5-methyl-4-phenylthiazol-2-yl)acetamide (4c) showed high selectivity, and whose IC50 value was determined as 23.30 ± 0.35 µM and >1000 µM against A549 human lung adenocarcinoma cells and NIH/3T3 mouse embryoblast cell lines, respectively. 2-[(1-Methyl-1H-imidazol-2-yl)thio]-N-(5-methyl-4-phenyl thiazol-2-yl)acetamide (4a) and 2-[(1-Methyl-1H-tetrazol-5-yl)thio]-N-(5-methyl-4-phenyl thiazol-2-yl)acetamide (4c) exhibited the highest apoptosis percentage among those tested, but not as high as the standard, cisplatin. [ABSTRACT FROM AUTHOR]

Regioselective synthesis of some triazole derivatives4–18was achieved from the versatile, readily accessible 4-phenyl-5-(quinolin-8-yloxy)methyl-4H-1,2,4-triazole-3-thiol/thione3.The structures of the newly synthesized products were confirmed and characterized by IR,1H NMR,13C NMR, and mass spectral studies. Most of the synthesized compounds were evaluated for their antitumor and antioxidant activities and demonstrated potent to weak activities. [ABSTRACT FROM PUBLISHER]

Novel rel-(6R,7R)-2-oxo-7-phenyl-3,5,6,7-tetrahydro-2H-thiopyrano[2,3-d]thiazole-6-carbaldehydes were synthesized via regio- and diastereoselective hetero-Diels-Alder reaction of 5-arylidene-4-thioxo-2-thiazolidinones with acrolein. The synthesized compounds were evaluated for anticancer and antiviral activities by the National Institutes of Health (NIH) following US NCI and AACF protocols. Anticancer activity screening on NCI60 cell lines allowed identification of 7-phenyl-2-oxo-7-phenyl-3,5,6,7-tetrahydro-2H-thiopyrano[2,3-d]thiazole-6-carbaldehyde3awith the highest level of antimitotic activity against leukemia with mean GI50/TGI values 1.26/25.22 μM. The screening of antiviral activity lead to identification of 7-(4-methoxyphenyl)-2-oxo-3,5,6,7-tetrahydro-2H-thiopyrano[2,3-d]thiazole-6-carbaldehyde3bwith a promising influence on EBV virus (EC50= 0.07 μM, SI = 3279) and moderate effect on Herpes simplex virus type 1 and Varicella zoster virus and 7-[4-(benzyloxy)phenyl]-2-oxo-3,5,6,7-tetrahydro-2H-thiopyrano[2,3-d][1,3]thiazole-6-carbaldehyde3ewith a promising influence on Hepatitis C virus (EC50= 12.6 μM, SI = 43.1). [ABSTRACT FROM AUTHOR]

Several structural types of thiazoloindoles can be distinguished with regard to the position of the fusion between the thiazole, benzene, and pyrrole rings. The present review describes the synthetic routes to five selected types of thiazoloindole derivatives with [3,2-a], [3,4-a], [5,4-b], [5,4-e], and [4,5-e] fusion. These compounds are useful for the discovering of future targets and the development of new drug molecules. [ABSTRACT FROM AUTHOR]

Thiazoles are important heterocyclic compounds which have many biological activities and different applications such as useful ligands, in optical sensors, etc. A literature survey shows that there are different routes to thiazoles. One of the most frequently used synthetic approaches consists of a reaction between α-halocarbonyl compounds with a CSNH2moiety. In this mini-review we have classified the contents based on the reagent or material providing the sulfur atom of the thiazole ring. Also, among many articles which have been devoted to thiazole syntheses here we presented some synthetic approaches published from 2012 to 2014. [ABSTRACT FROM AUTHOR]

A novel and facile method for the direct sulfenylation of 2,3-dihydroimidazo[2,1-b]thiazoles with disulfides has been developed. The transformation is promoted by iodine under metal-free conditions, providing the corresponding products in moderate to good yields. [ABSTRACT FROM PUBLISHER]

The current review article presents the available synthetic profiles for the preparation of different types of thiazoloquinolines. The classification of thiazoloquinolines into nine types is based on the position of the linkage between the thiazole and the quinolines rings. [ABSTRACT FROM PUBLISHER]

4,4′-Dimonochloroacetyl diphenylselenide (2) was prepared as a new precursor for the title studies by chloroacetylation of diphenylselenide (1).2interacts with thiourea to afford 4,4′-di(2″-aminothiazol-4″-yl)diphenylselenide (3). Condensation of3with aromatic aldehydes in the presence of a catalytic amount of dry piperidine furnished aldimines (4). Interaction of4with mercaptoacetic acid afforded 4,4′-di(2″-(2‴-substituted phenyl-3‴-thiazolo-4‴-thiazolidinon)-3‴-yl)diphenylselenides (6). Schiff bases4interact with mono chloroacetyl chloride in dry dioxane and triethylamine produced 4,4′-di(2″-(4‴-substituted phenyl-3‴-chloro-2‴-azetidinon-1‴-thiazolo)-1‴-yl)diphenylselenides (8). 1,3-Dipolar cyclonucleophilic addition of diazomethane to certain of4gave 4,4′-di(2″-(5‴-substituted phenyl-Δ2-1‴,2‴,3‴-triazoline thiazolo)-1‴-yl)diphenylselenides (10).2interacts with secondary heteroalicyclic amines to afford 4,4′-diglycyl diphenylselenides (11). The structures of the synthesized compounds are based on correct physical data, IR,1H NMR,13C NMR, and by chemical means. Some of the synthesized compounds were biologically tested. [ABSTRACT FROM PUBLISHER]

The synthesis of novel heterocyclic aryl monoazo organic compounds, including 3-amino-4,6-dimethyl-N-(5-arylazothiazol-2-yl)selenopheno[2,3-b]pyridine-2-carboxamide, 3-amino-4,6-diphenyl-N-(5-arylazothiazol-2-yl)selenopheno[2,3-b]pyridazine-2-carboxamide and 3-amino-5,6,7,8-tetrahydro-4-(4-methoxyphenyl)-N-(5-arylazothiazol-2-yl)selenopheno[2,3-b]quinoline-2-carboxamide using a condensation reaction involving different 2-(N-chloroacetyl)-5-arylazo-thiazole derivatives with seleno derivatives of pyridine, pyridazine, and/or quinolone, respectively, was undertaken. Analytical and spectroscopic data confirm the proposed structures. The novel synthesized thiazole-selenium disperse dyes were applied for dyeing polyester fabrics. Color characteristics and fastness properties were investigated. The novel synthesized compounds exhibited high efficiency based on in vitro screening of their antioxidant activity, antitumor activity against Ehrlich ascites carcinoma cell EACC cell line and antimicrobial activity against various pathogenic bacteria and fungi. The colored polyester fibers could be applied as sterile and/or biological active fabrics used in various life applications. [ABSTRACT FROM AUTHOR]

Treatment of 2-aminothiazole (1) with triselenium dicyanide (2) afforded selenocyanate (3). Reduction of3with NaBH4gave the diselenide4. Compounds3and4were used as a key intermediate for the synthesis of a series of 2-amino-5-selenothiazoles. The newly synthesized compounds were evaluated as anti-inflammatory and analgesic agent. [ABSTRACT FROM AUTHOR]

Methods for the preparation of various fused pyrazolothiazoles were reviewed here for the first time. The main types of fused pyrazolothiazole are pyrazolo[5,1-b]thiazoles, pyrazolo[3,4-d]thiazoles, and pyrazolo[4,3-d]thiazoles. Some research and industrial application of pyrazolothiazoles are reported. [ABSTRACT FROM PUBLISHER]

5,7-Dimethyl-3H-thiazolo[4,5-b]pyridine-2-one was obtained under the reaction of 4-iminothiazolidin-2-one with acetylacetone. Further structural modifications include the introduction of diversity at the N3and C6positions. The antioxidant activity of the synthesized compounds was evaluated in vitro by the method of scavenging effect on 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals. [Supplemental materials are available for this article. Go to the publisher's online edition ofPhosphorus, Sulfur, and Silicon and the Related Elementsto view the following free supplemental files: Additional figures] [ABSTRACT FROM AUTHOR]

A simple, efficient, and environmentally benign methodology has been accomplished for the synthesis ofα-aminophosphonates by one-pot three-component reaction of ethyl-2-amino-α-(methoxy-imino)-4-thiazoleacetate, aldehydes, and diethylphosphite by using Amberlyst-15 as catalyst at room temperature under solvent-free conditions. Their chemical structures were characterized by infrared (IR), NMR (1H,13C &31P), mass spectral, and elemental analysis. All the title compounds were screened for radical-scavenging activity by 1,1-diphenyl-2-picrylhydrazyl (DPPH), nitic oxide (NO), and hydrogen peroxide (H2O2) methods. Supplementary materials are available for this article. Go to the publisher's online edition ofPhosphorus, Sulfur, and Silicon and the Related Elementsfor the following free supplemental files:Additional text and figures. [ABSTRACT FROM AUTHOR]

A novel series of 1-((4-methyl-2-substituted thiazol-5-yl)methyleneamino)-2-substituted isothiourea derivatives was synthesized by alkylation of (Z/E)-1-((4-methyl-2-substituted thiazol-5-yl)methylene)thiosemicarbazide with alkylhalide in acetone. All the newly synthesized compounds were characterized by spectral (IR,1H NMR,13C NMR, and mass spectrometry) methods. The newly synthesized compounds were screened for in vitro antimicrobial activity. Most of the compounds show moderate to excellent antimicrobial activity. [Supplementary materials are available for this article. Go to the publisher's online edition ofPhosphorus, Sulfer, and Silicon and the Related Elementsfor the following free supplemental files:Additional figures and tables.] [ABSTRACT FROM PUBLISHER]

An electrochemically induced catalytic crossed Aldol condensation of one equivalent of rhodanine with various aromatic aldehydes and ketones in ethanol in an undivided cell in the presence of sodium bromide as an electrolyte results in the formation of the corresponding 5-arylalkylidenerhodanines in 80–96% yield with reactions in 40 min. Supplemental materials are available for this article. Go to the publisher's online edition ofPhosphorus, Sulfur, and Silicon and the Related Elementsto view the free supplemental file. [ABSTRACT FROM AUTHOR]

3H-Benzothiazole-2-thione and 3H-benzoxazole-2-thione were selectively S-alkylated by use of O-alkylisoureas as the alkylating reagents. The reactions could be performed under mild reaction conditions in short reaction times, and high yields were obtained using O-primary-alkylisoureas, whereas low yields were obtained with sec- and tert-alkylisoureas. [ABSTRACT FROM PUBLISHER]

A simple, inexpensive, and efficient one-pot synthesis of 2-arylthiazoline derivatives under solvent-free conditions using a catalytic amount of 1-butyl-3-methylimidazolium tribromide with excellent product yields is reported. This methodology provides easy, quantitative access to various 2-arylthiazoline derivatives, using environmentally benign 1-butyl-3-methylimidazolium tribromide as a catalyst. GRAPHICAL ABSTRACT [ABSTRACT FROM AUTHOR]

The compounds {[4-(3-methyl-3-aryl(mesityl-phenyl-tetralino)cyclobutyl)-1,3-thiazol-2-yl]amino}(aryl)methyl-phosphinic acids 2a–l were prepared by condensation of 2-amino-4-(3-aryl(mesityl-phenyl-tetralino)-3-methylcyclobutyl) thiazoles 1a–c with various aromatic aldehydes and hypophosphorous acid through a one-pot reaction. The characterizations of these compounds were obtained by elemental analyses, infrared (IR) spectra, and 1H, 13C, and 31P NMR (nuclear magnetic resonance) techniques. The synthesized compounds were tested in vitro against one Gram-positive and two Gram-negative bacterial strains, one mycobacterial strain, and a fungus Candida albicans. Compound 2f showed significant activity against Staphylococcus aureus, whereas the others had no remarkable activity on this strain. Compound 2g was found to be more active than the others against Mycobacterium fortuitum at an MIC (minimum inhibitory concentration) value of 32 μg/mL. The antibacterial and antifungal activities of 2a–l were also compared with various standard drugs. [Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements for the following free supplemental resource: Biological Activities. Table S1. Figures S1–S6.] GRAPHICAL ABSTRACT [ABSTRACT FROM AUTHOR]

Synthesis of polyfunctionalized ketenimines via three-component reactions of rhodanine and 5-(4-dimethylaminobenzylidene)-rhodanine with dialkyl acetylenedicarboxylates and alkyl isocyanides is described. The reactions proceed smoothly under mild conditions leading to the desired products in good yields. In the case of methyl acetylenecarboxylate, the reaction led to methyl (Z)-3-({5-[(E)-1-(tert-butylamino)methylidene]-4-oxo-4,5-dihydro-1,3-thiazol-2-yl}sulfanyl)-2-propenoate in low yield. GRAPHICAL ABSTRACT [image omitted] [ABSTRACT FROM AUTHOR]

A series of novel 1,3-thiazoline derivatives containing a 5- or 6-position halogenated indole moiety were synthesized via a one-pot and three-step reaction. Their structures were confirmed by spectroscopic methods. The fungicidal activities of all the title compounds were evaluated. Most of them exhibited moderate to high activity against eight plant pathogens at the concentration of 50 ug/mL. Generally the fungicidal activity of fluorinated indolyl thiazolines was higher than that of chlorinated indolyl thiazoline derivatives. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. GRAPHICAL ABSTRACT [image omitted] [ABSTRACT FROM AUTHOR]

The reaction of 4,5-diphenyl-2-propargylmercaptoimidazole with various aryl iodides catalyzed by Pd-Cu in the presence of triethylamine as base in dimethyl formamide (DMF) leads to the formation of 3-aryl-substituted imidazo[2,1-b]thiazoles. [ABSTRACT FROM AUTHOR]

A mild and selective procedure for the synthesis of 4-carboxy thiazoles and thiazolidines starting from naturally occurring cysteine by condensation with aldehydes is described. The optimized procedure, taking advantage of the positive effect of microwave irradiation on the MnO2-mediated oxidation step, is suitable for multigram scale. Coordination of these ligands towards a variety of transition metal ions gave new interesting metallorganic supramolecular architectures in which an extensive 3D network is created through hydrogen bonding. [ABSTRACT FROM AUTHOR]

A novel, one-pot, multicomponent synthesis of 4-arylidene-3-methyl-1-(4-arylthiazol-2-yl)-1H-pyrazol-5(4H)-ones is described using phenacyl bromides, thiosemicarbazide, ethylacetoacetate, and aryl aldehydes. This synthesis involves simultaneous formation of two heterocycles like thiazole and pyrazolone along with condensation of active methylene group by aldehydes via Knoevenagel reaction. The methodology is mild, efficient, and high yielding. GRAPHICAL ABSTRACT[image omitted] [ABSTRACT FROM AUTHOR]

An efficient and facile synthesis of 2,4-disubstituted thiazoles is achieved by a one-pot reaction of aldehydes and α-bromoketones with thiosemicarbazide by grinding under catalyst- and solvent-free conditions. This method has notable advantages in terms of simple workup, neat conditions, high yield, reasonably rapid reaction rate, and environmental friendliness. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. GRAPHICAL ABSTRACT[image omitted] [ABSTRACT FROM AUTHOR]

Thirteen new (3,4-diaryl-3H-thiazol-2-ylidene)pyrimidin-2-yl amine derivatives were synthesized by reacting 1-aryl-3-pyrimidin-2-yl-thiourea derivatives and phenacyl bromides in absolute ethanol. The solid that separated was filtered and recrystallized from ethanol. The structures of the synthesized compounds were confirmed by elemental analyses and 1H NMR, 13C NMR, and EI-MS spectral data. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. GRAPHICAL ABSTRACT[image omitted] [ABSTRACT FROM AUTHOR]

In this study, several new 1-(4-aryl-5-triazolyl-2-thiazolyl)-3,5-diaryl-2-pyrazolines (3a-r) were synthesized by reacting 3,5-diaryl1-thiocarbamoyl-2-pyrazolines (1) with 2-bromo-1-aryl-2-(1H-1,2,4-triazol-1-yl) ethanones (2) in boiling ethanol. The chemical structures of the compounds were verified by IR, 1H NMR, ESI-MS spectroscopic data, and elemental analyses. GRAPHICAL ABSTRACT[image omitted] [ABSTRACT FROM AUTHOR]

A simple synthesis of dialkyl (2,3-dihydro-1,3-thiazol-2-yl)-phosphonates from thiazolium salts and trialkyl phosphites is described. The series of dialkyl (2,3-dihydro-1,3-thiazol-2-yl)-phosphonates with various substituents in positions 3, 4, and 5 of the thiazole ring were prepared. However, only phosphonates with an aryl on the nitrogen atom were stable enough for chromatographic purification, although all the new phosphonates are very sensitive to oxidation. We made efforts to apply dialkyl (2,3-dihydro-1,3-thiazol-2-yl)-phosphonates in a Horner-Wadsworth-Emmons reaction, but the generated antiaromatic anion of phosphonate decomposed quickly, even at -70°C. GRAPHICAL ABSTRACT[image omitted] [ABSTRACT FROM AUTHOR]

A simple, one-pot synthesis of N-(4-aryl-3-alkylthiazol-2(3H)-ylidene)anilines and N-(4-aryl-3-alkylthiazol-2(3H)-ylidene)benzamides via the reaction of primary alkylamines, α-bromoketones, and phenylisothiocyanate or benzoylisothiocyanate is described. GRAPHICAL ABSTRACT[image omitted] [ABSTRACT FROM AUTHOR]

An improved green procedure for the synthesis of 2-aryl- and 2-hetarylbenzothiazoles by condensation of equivalent amounts of 2,2'-diaminodiphenyldisulfides or 2-aminothiophenols and various aromatic aldehydes in PEG 200/400 under microwave irradiation has been developed. This method allows the synthesis of 2-arylbenzothiazoles in high yields and with high purity regardless of the state of the starting compounds (liquid or solid) or the nature of the substituents in the aromatic ring. [ABSTRACT FROM AUTHOR]

ω-(2-Aryl-4-oxothiazolidin-3-yl)alkylphosphonic acids are prepared in an easy workup procedure by the addition of methyl mercaptoacetate to in situ-generated arylideneaminoalkyl phosphonic acids. [ABSTRACT FROM AUTHOR]

A series of benzoxazole and benzothiazoles was readily prepared from the reaction of ortho-aminophenol/ortho-aminothiophenol and aldehydes using solid silica supported ferric chloride (SiO2-FeCl3) as catalyst followed by oxidation with H2O2 under ambient conditions. Some of advantages of this method are a simple and convenient procedure, easy purification, and shorter reaction times. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. [ABSTRACT FROM AUTHOR]

A series of novel α-amino phosphonate derivatives containing the thiazole and pyrazole moieties 3 were synthesized by the Mannich-type reaction of substituted pyrazole-aldehyde 1, 2-amino-5-ethoxycarbonyl-4-methyl-thiazole 2, and dialkyl phosphites or triphenyl phosphite in the presence of a Lewis acid such as magnesium perchlorate as the catalyst under solvent-free conditions. Their structures were clearly confirmed by spectroscopy data (IR, 1H NMR, 31P NMR, MS) and elemental analysis. The results of a preliminary bioassay (in vitro) indicated that some of the title compounds 3 possessed moderate herbicidal activities against dicotyledonous plants (Brassica campestris L) or monocotyledonous plants (Echinochloa crus-galli) at the concerntration of 100 mg/L. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. [ABSTRACT FROM AUTHOR]

A new series of N-thiazole, 3-phenyl, 4-substituted phenyl azetidine-2-ones 4(a-h) have been synthesized in good yields starting from 2-aminothiazole 1. In the first step, then Schiff's bases 3(a-h) are prepared by the condensation of 2-aminothiazole 1 with different aryl aldehydes 2(a-h). Finally, monocyclic β-lactams, i.e. substituted azetidinones 4(a-h), were the products formed using three different methods by the dehydrative cyclocondensation of 3(a-h) with phenyl acetyl chloride in dioxane, phenyl acetic acid-thionyl chloride in dichloromethane and phenyl acetic acid-phosphorus oxychloride in dichloromethane in the presence of triethylamine. We found that latter method is the best as compared with the former two methods. The synthesized molecules 4(a-h) were screened for their antibacterial activity against four microorganisms: Staphylococcus aureus (Gram positive), Pseudomonas vulgaris (Gram positive), Pseudomonas aeruginosa (Gram negative), and Escherichia coli (Gram negative). Their antibacterial activities are reported, and on the basis of the screening data available, attempt is also made to elucidate the structure-activity relationship. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. [ABSTRACT FROM AUTHOR]

2-Ethoxycarbonylmethylidine-4,5-dihydro-4-thiazolinone (1) was condensed with bis aromatic aldehydes such as terephthalaldehyde or 4,4'-bisformyl-diphenylether (2a,b) (2:1 molar ratio) and furnished bis-4-thiaozlidinones (3a,b). The reaction of (3a,b) with malononitrile and aromatic aldehydes (1:2:2 molar ratio) gave bis thiazolopyridines (4a-d). Bis-(thiazolopyridine) derivative (6) was obtained by reaction of 4-thiaozlinone (5c) with bis aldehyde (2b) in refluxing ethanol containing piperidine. Cyclization of 4-thiazolinones (5a,b) with different α-cyanocinnamonitriles gave thiazolo[3,2-a]pyridines (7a-d). Compound 9 was produced via the reaction of 8 with thioglycolic acid, which reacted with p-chlorobenzaldehyde to produce 10. Compound 10 was condensed with hydrazine hydrate and afforded 11. Compounds 12 and 16a,b were produced by the reaction of 9 with isatin and α-ethoxycarbonylcinnamonitriles, respectively. [ABSTRACT FROM AUTHOR]

2,4,6-Substituted 1,3,5-tris(benzothiazolyl)hexahydro-1,3,5-triazine derivatives were synthesized by the condensation of substituted benzothiazoles with aldehydes by conventional as well as by microwave irradiation (solvent free and solid supported) methods. All compounds were tested for antibacterial and antifungal activities, and the results have been compared with standard drugs. Acaricidal and anti-feedant activities were also tested. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. [ABSTRACT FROM AUTHOR]

2-Cyano-N-(9,10-dioxo-9,10-dihydro-anthracen-2-yl)-acetamide (1) was utilized as a key intermediate for the synthesis of thiazolidin-4-one 2 and thiocarbamoyl 5 derivatives via reaction with 2-sulfanylacetic acid and phenyl isothiocyanate, respectively. Compound 5 reacted with different α-halo compounds to give thiazolidin-5-one 4, thiazolidine 7a,b, thiazolidin-4-one 8, and thiophene derivatives 10a,b. Thiazoline 6 and tetrahydro-benzothiophene 12 derivatives were obtained via a one-pot reaction of compound 1 with phenyl isothiocyanate/sulfur and cyclohexanone/sulfur, respectively. Representative compounds of the synthesized products were evaluated as antimicrobial agents. Some of these compounds exhibited promising activities. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. [ABSTRACT FROM AUTHOR]

A series of fluorinated 2-(N-arylamino)-4-arylthiazoles (3) was synthesized by the condensation of appropriate arylthioureas (2) with corresponding α-bromoacetophenones (1) by using “green chemistry” techniques, viz. mechanochemical mixing and microwave or ultrasonic irradiation. Compared with conventional procedures, the reaction can be carried out under milder conditions, requiring a shorter reaction time and giving higher yields following the green chemistry methodology. All the synthesized compounds were characterized on the basis of elemental analyses and spectral data (IR, 1H NMR, and mass spectrometry). Representative compounds were also evaluated for their insecticidal activity against Helicoverpa armigera, and some of them showed promising activity. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. [ABSTRACT FROM AUTHOR]

1-(2-(4,5-Dihydro-3-(4-methyl-2-phenylthiazol-5-yl)-5-phenylpyrazol-1-yl)-4-substituted thiazol-5-yl)-2-phenyldiazene were synthesized from hydrazonoyl halides and 3-(4-methyl-2-phenyl-1,3-thiazol-5-yl)-5-phenyl-4,5-dihydro-1H-pyrazole-1-carbothioamide in ethanolic triethylamine. Also, pyrazolo[5,1-a]pyrimidines, 2,3,6-trisubstituted pyridines, and pyrazolo[3,4-d]pyridazines were obtained from sodium salt of 3-hydroxy-1-(4-methyl-2-phenylthiazol-5-yl)prop-2-en-1-one and different heterocyclic amines. All structures of the newly synthesized compounds were elucidated by elemental analysis, spectral data, and alternative synthetic route whenever possible. The newly synthesized compounds were tested towards different microorganisms. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. [ABSTRACT FROM AUTHOR]

Some novel thiophenes (4a,b, 5, and 9a,b) were obtained from the cycloalkylation of the thiocarbamoyl group in the cyanothioacetanilide derivative (1) with α-halocarbonyl compounds. Also, the reaction of cyanothioacetanilide derivative with phenyl isothiocyanate in the presence of potassium hydroxide followed by in situ heterocyclization of the resulting adduct with α-halocarbonyl compounds furnished the corresponding thiazole (12, 14, and 15), pyrazole (19), and pyraozlo[1,5-a]pyrimidine (22, 25, and 26) derivatives. Compounds (4b, 5, 9a, 12, 13, 18, 22, 25, and 26) were tested to evaluate their antimicrobial activity. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. [ABSTRACT FROM AUTHOR]

Cyanobenzothiazole (1) was utilized for the synthesis of several new fused and 2-heterylbenzothiazole derivatives such as pyrimido, pyridino, quinolino, pyrazolopyranyl, pyrimidinopyranyl, and cyclohexanopyranyl benzothiazole derivatives. [ABSTRACT FROM AUTHOR]

A convenient method for the synthesis of thiazoles by treatment of α-bromoketones with thioamides (Hantzsch synthesis) in the absence of catalysts under microwave irradiation has been developed. The products were formed rapidly in excellent yields. An efficiency comparison of time, yield, and effort clearly proved the microwave technique to be superior. The structures of the newly synthesized compounds were characterized by spectroscopic data and elemental analyses. The synthesized compounds were tested for their biological activity. Depending on the substituents, some of the thiazoles exhibit very good antibacterial or antifungal activity. [ABSTRACT FROM AUTHOR]

2,4,6-Trichloro 1,3,5-triazine was selectively reacted with new nucleophilic reagents such as 4-methoxy-2-aminobenzothiazole, 2-chloro-4-trifluoromethyl-aniline, and phenylsubstituted thiourea in alkaline medium to give 2-(4-methoxybenzothiazol-2'-ylamino)-4-(phenylthioureido)-6-(substitutedthioureido)-1,3,5-triazines. The structures of these compounds were confirmed by IR, 1H NMR, 19F NMR, mass spectral data, and elemental analysis. The compounds show fungicidal activity against Alternaria alternata, Aspergillus niger, and Macrofomina. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. [ABSTRACT FROM AUTHOR]

2-Substituted benzothiazoles have been efficiently synthesized in good yields by the condensation reaction of o-aminothiophenol with aldehydes in the presence of a catalytic amount of perchloric acid-doped polyaniline (HClO4/PANI). The low cost, simple recovery, and efficient reusability are remarkable characteristics of this catalyst. [ABSTRACT FROM AUTHOR]

A series of hydrazinothiazoles has been synthesized by the condensation of thiosemicarbazones and α-bromoketones. Similarly the hydrazinothiazolidiones were prepared by the condensation of thiosemicarbazone and α-bromoesters. The newly synthesized compounds were characterized by NMR and LCMS studies. [ABSTRACT FROM AUTHOR]