2362-69-8

Upstream product

• 108-86-1 bromobenzene 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 99-90-1 para-bromoacetophenone 
• 100-46-9 benzylamine 
• 4209-02-3 1-(4-bromophenyl)-2-chloroethan-1-one 
• 2227-79-4 benzenecarbothioamide 
• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 98475-05-9 α-tosyloxy-4-bromoacetophenone 
• 99-73-0 para-bromophenacyl bromide 

Downstream Products

• 951000-53-6 C₁₅H₉BrClNS 
• 951000-49-0 C₁₅H₉BrFNS 

Relevant academic research and scientific papers

A combine approach of chemical synthesis, biological evaluation and structural dynamics studies revealed thiazole substituted arylamine derivatives as potent FabH enzyme inhibitors

Bacterial FabH enzyme is a broad-spectrum antimicrobial target and can be used in the design of novel antibiotics. This study reports chemical synthesis of thiazole based amine compounds as FabH inhibitors, followed by biological evaluation, and computati

Preparation method of 2, 4-disubstituted thiazole compound

The invention discloses a preparation method of a 2, 4-disubstituted thiazole compound. The method comprises the following steps: carrying out heating reflux reaction on substituted carboxylic acid inthionyl chloride to obtain yellow transparent liquid, and adding dichloromethane to dilute for later use; in an ice bath, slowly dropwise adding the substituted acyl chloride solution into ammonia water while stirring, stirring at room temperature to separate out a white solid, and after the reaction is finished, carrying out suction filtration, washing and drying to obtain substituted amide; carrying out reflux on substituted amide and Lawesson in tetrahydrofuran, carrying out rotary evaporation to remove the solvent after the reaction is finished, and carrying out column purification on thecrude product to obtain substituted sulfamide. The preparation method comprises the following steps: putting substituted sulfamide, ethanol, triethylamine and an alpha-bromocarbonyl compound into a pressure reaction tank, putting the pressure reaction tank into an annular focusing single-mode microwave synthesizer for irradiation, and cooling with compressed air to obtain a target compound. Basedon microwave synthesis, the invention has the advantages of short reaction time, high yield, high heating speed, environment friendliness and the like, and provides a microwave synthesis method of a2, 4-disubstituted thiazole compound.

Br?nsted acid-promoted thiazole synthesis under metal-free conditions using sulfur powder as the sulfur source

A Br?nsted acid-promoted sulfuration/annulation reaction for the one-pot synthesis of bis-substituted thiazoles from benzylamines, acetophenones, and sulfur powder has been developed. One C-N bond and multi C-S bonds were selectively formed in one pot. The choice of the Br?nsted acid was the key to the high efficiency of this transformation under metal-free conditions.

One-Pot Preparation of Aromatic Amides, 4-Arylthiazoles, and 4-Arylimidazoles from Arenes

Simple treatment of arenes with α-bromoacetyl chloride and AlCl3, followed by the reaction with molecular iodine and aq. NH3, thioamides, or amidines gave the corresponding primary aromatic amides, 4-arylthiazoles, or 4-arylimidazoles in good yields, respectively. Aryl α-bromomethyl ketones are the key intermediates in those reactions. Primary aromatic amides were formed from arenes through the reaction of aryl α-bromomethyl ketones with molecular iodine and aq. NH3, and 4-arylthiazoles and 4-arylimidazoles were formed from arenes through the reactions of aryl α-bromomethyl ketones with thioamides and amidines, respectively, in one pot under transition-metal-free conditions.

Mild Homologation of Esters through Continuous Flow Chloroacetate Claisen Reactions

The selective chloromethylenation of functionalized esters using chloroacetic acid (CA) and LiHMDS (HMDS=hexamethyldisilazide) in a continuous-flow setup is reported. This Claisen homologation is for the first time extended to bis-chloromethylenation using dichloroacetic acid (DCA), thus giving access to under-explored α,α′-bis-chloroketones. The use of flow conditions enables efficient generation and reaction of the unstable chloroacetate dianion intermediates, leading to unprecedented mild and scalable reaction conditions at an economical reagent stoichiometry (?10 °C, 1 min, 1.0–2.4 equiv dianion). The clean reaction profiles allow subsequent use of the unpurified crude products, which is demonstrated in the synthesis of various heterocycles of broad interest. Furthermore, we report a novel, catalyst-free substitution of the obtained monochloro ketone products with (hetero)aryl zinc enolates to give valuable 1,4-diketones.

Syntheses of biodynamic heterocycles: baker’s yeast-assisted cyclocondensations of organic nucleophiles and phenacyl chlorides

Substituted phenacyl chlorides (1a–f) were cyclocondensed with nucleophiles thiourea (2a) and thiobenzamide (2b) in presence of baker’s yeast (Saccharomyces cerevisiae) as whole-cell enzyme source in acetonitrile at room temperature to obtain 4-(4-substituted phenyl)thiazol-2-amines (3a–f) and 4-(substituted phenyl)-2-phenylthiazoles (4a–f), respectively. Moreover, substituted phenacyl chlorides also reacted with nucleophiles 2-amino-1,3,4-thiadiazole (2c), o-phenylenediamine (2d), 1-amino-2-mercapto-5-phenyl triazole (2e), and pyridin-2-amine (2f) at room temperature in presence of baker’s yeast to give fused heterocycles 6-(4-substituted phenyl)-2-phenylimidazo[2,1-b][1,3,4]thiadiazoles (5a–f), 2-(4-substituted phenyl)quinoxalines (6a–f), 6-(4-substituted phenyl)-3-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines (7a–f), and 2-(4-substituted phenyl)H-imidazo[1,2-a]pyridines (8a–f), respectively. The experimental conditions for these cyclocondensations were optimized to obtain the biodynamic heterocycles in high yield. The unique features of this work are use of baker’s yeast as a cheap and readily available natural source of biocatalyst, noticeable rate acceleration, convenient route to products, cost effectiveness, and scalability.

One pot synthesis of substituted imidazopyridines and thiazoles from styrenes in water assisted by NBS

Heating of commercially available styrenes with NBS in water followed by reaction with 2-aminopyridines or thioamides afforded important heterocyclic scaffolds in a one pot procedure. The reaction proceeds via co-oxidant free, in situ formation of α-bromoketone using NBS as a bromine source as well as an oxidant followed by trapping with suitable nucleophiles to provide imidazopyridines and thiazoles.

Synthesis of thiazoles and aminothiazoles from β-keto tosylates under supramolecular catalysis in the presence of β-cyclodextrin in water

This is the first report on the supramolecular synthesis of thiazoles/aminothiazoles from β-keto tosylates and thioamide/thiourea in water in the presence of β-cyclodextrin in impressive yields. Formation of inclusion complexes was explained from 1H NMR studies. Copyright Taylor & Francis Group, LLC.

Nuclear fluorination of 2,4-diarylthiazoles with Accufluor

A series of 2,4-diphenylthiazole derivatives were synthesized and directly fluorinated at the 5-position by reaction with the N-F fluorinating reagent Accufluor. Although fluorination occurred selectively at the thiazole ring, it was always inc

Aqueous phase synthesis of thiazoles and aminothiazoles in the presence of β-cyclodextrin

A simple and practical procedure for the aqueous phase preparation of thiazoles and aminothiazoles has been developed from phenacyl bromides and thioamide/thiourea in the presence of β-cyclodextrin.