19968-59-3

Upstream product

• 62-55-5 thioacetamide 
• 2114-00-3 2-bromo-1-phenyl-1-propanone 
• 60-35-5 acetamide 
• 1826-16-0 2-methyl-4-phenylthiazole 
• 333-27-7 methyl trifluoromethanesulfonate 
• 5650-40-8 2-hydroxypropiophenone 
• 2157-50-8 propiophenone oxime 
• 108-24-7 acetic anhydride 
• 14229-62-0 S-1-methyl-2-oxo-2-phenylethyl thioacetate 
• 70-11-1 α-bromoacetophenone 
• 93-55-0 1-phenyl-propan-1-one 

Downstream Products

• 95875-52-8 2,3,5-trimethyl-4-phenyl-thiazolium; iodide 
• 25021-47-0 2,5-dimethyl-4-(4-nitro-phenyl)-thiazole 
• 25020-83-1 1,3-bis-[4-(2,5-dimethyl-thiazol-4-yl)-phenyl]-thiourea 
• 7021-89-8 1-[4-(2,5-dimethyl-thiazol-4-yl)-phenyl]-3-(4-pentyloxy-phenyl)-thiourea 
• 7021-87-6 1-(4-butoxy-phenyl)-3-[4-(2,5-dimethyl-thiazol-4-yl)-phenyl]-thiourea 
• 7021-88-7 1-[4-(2,5-dimethyl-thiazol-4-yl)-phenyl]-3-(4-isobutoxy-phenyl)-thiourea 
• 3544-45-4 1-[4-(2,5-dimethyl-thiazol-4-yl)-phenyl]-3-(4-propoxy-phenyl)-thiourea 
• 7021-86-5 1-[4-(2,5-dimethyl-thiazol-4-yl)-phenyl]-3-(4-isopropoxy-phenyl)-thiourea 
• 7021-84-3 1-[4-(2,5-dimethyl-thiazol-4-yl)-phenyl]-3-(4-ethoxy-phenyl)-thiourea 
• 7021-83-2 1-[4-(2,5-dimethyl-thiazol-4-yl)-phenyl]-3-(4-methoxy-phenyl)-thiourea 
• 25021-58-3 4-(2,5-dimethyl-thiazol-4-yl)-aniline 
• 100259-09-4 2-(4-dimethylamino-styryl)-3,5-dimethyl-4-phenyl-thiazolium; iodide 

Relevant academic research and scientific papers

Access to Thiazole via Copper-Catalyzed [3+1+1]-Type Condensation Reaction under Redox-Neutral Conditions

A new strategy for thiazoles via copper-catalyzed [3+1+1]-type condensation reaction from oximes, anhydrides and potassiumthiocyanate (KSCN) is developed herein. The transformation has good functional group tolerance and various thiazoles were formed smoothly in good to excellent yields under mild reaction conditions. This process involves copper-catalyzed N-O/C-S bond cleavages, activation of vinyl sp2 C-H bond, and C-S/C-N bond formations which are under redox-neutral conditions as well as operational simplicity.

Exploration and Optimization of an Efficient One-pot Sequential Synthesis of Di/tri-substituted Thiazoles from α-Bromoketones, Thioacids Salt, and Ammonium Acetate

Exploration of scope of an optimized one-pot sequential procedure for preparing of 2,4-di- and 2,4,5-tri-substituted thiazoles has been accomplished. The synthesis was performed by the initial formation of a β-keto-thioester intermediate from nucleophilic substitution of α-bromoketones with thioacid potassium salts, followed by treatment with ammonium acetate and one equivalent of acetic acid in toluene to form imine intermediate eventually leading to cyclization yielding thiazoles. This procedure should be highlighted with a flexible way to control the substitution pattern around thiazole ring by choosing appropriately substituted α-bromoketones even containing acid labile functionality and thioacid potassium salts, and thus its applicability is very wide.

Liquid-phase organic synthesis of thiazoles using poly(ethylene glycol)-bound sulfonyl chloride resin

Reaction of poly(ethylene glycol) (PEG)-bound sulfonic acid with thionyl chloride formed difunctionalized PEG-bound sulfonyl chloride, which was treated with α-hydroxyketones, followed by treatment with thioamides in the presence of potassium carbonate, to afford thiazoles in good yields with a facile workup procedure. Copyright Taylor & Francis Group, LLC.

Use of a metallation reaction to obtain substituted 2-(5-methyl-2- thiazolyl)ethanols

The interaction of anions, obtained by treating 2,4,5-trimethylthiazole and 2,5-dimethyl-4-phenylthiazole with butyllithium, with aliphatic and aromatic aldehydes leads to substituted 2-thiazolyl-1-ethanols. It was established that the metallation reaction occurs at the 2-methyl group of the thiazoles. 2005 Springer Science+Business Media, Inc.

Environmentally benign preparation of heteroaromatics from ketones or alcohols, with macroporous polystyrenesulfonic acid and (diacetoxyiodo)benzene, followed by thioamide, amidine, and 2-aminopyridine

An operationally simple, efficient, and environmentally benign preparation of heteroaromatics such as thiazoles, imidazoles, and imidazo[1,2-a]pyridines from the reactions of a polymer-supported [hydroxy(sulfonyloxy)iodo]benzene (2) with ketones or alcohols, followed by treatment with thioamides, benzamidine, and 2-aminopyridine, respectively, in the presence of potassium carbonate were successfully carried out.

Selective lithiation of 2-methyloxazoles. Applications to pivotal bond constructions in the phorboxazole nucleus

(equation presented) R = Alkyl, Vinyl, Aryl 6:7 >95:5 The lithiation of 2-methyloxazoles with alkyllithium and hindered lithium amide bases generally results in the competitive formation of a mixture of 5-lithio-and 2-(lithiomethyl)oxazole isomers. Herein a synthetically useful lithiation method which allows for the selective formation of 2-(lithiomethyl)oxazole is described. Diethylamine has been found to be a kinetically competent proton source that will mediate the equilibration of the kinetically formed 5-lithiooxazole to its more stable 2-(lithiomethyl)oxazole counterpart. Application of this metalation strategy with lithium diethylamide to two important bond constructions relevant to a projected phorboxazole synthesis is presented.