102183-91-5

Upstream product

• 56177-37-8 1-(4-nitrophenyl)-2-(p-tolylsulfonyloxy)ethanone 
• 103-85-5 monophenylthiourea 
• 34006-49-0 2-chloro-1-(4-nitrophenyl)ethanone 
• 99-81-0 4-Nitrophenacyl bromide 
• 102183-93-7 2-imino-4-(4-nitrophenyl)-3-phenyl-2,3-dihydrothiazole 

Downstream Products

• 110960-43-5 4-(4-nitrophenyl)-2-(N-phenyl)trifluoroacetamidothiazole 

Relevant academic research and scientific papers

Sodium fluoride as an efficient catalyst for the synthesis of 2,4-disubstituted-1,3-thiazoles and selenazoles at ambient temperature

Sodium fluoride was found to be a simple, mild and efficient catalyst for the synthesis of 2,4-disubstituted 1,3-thiazoles and selenazoles utilizing phenacyl bromides/3-(2-bromoacetyl)-2H-chromen-2-one and thiourea/ phenylthiourea/selenourea in aqueous methanol at ambient temperature. Analytically pure products are formed within 1-3 min in excellent yields.

Visible light triggered, catalyst free approach for the synthesis of thiazoles and imidazo[2,1-: B] thiazoles in EtOH:H2O green medium

The development of a visible light promoted, mild and greener approach for the synthesis of highly functionalized thiazoles and imidazo[2,1-b]thiazoles under photochemical activation in EtOH:H2O green medium is demonstrated. The characteristic feature of the present protocol is the utilization of visible light (an omnipresent, nontoxic, environmentally benign and inexpensive reagent) to form C-S and C-N bonds and circumvent the use of catalysts or photosensitizers. The reported protocol is the first example of visible light promoted synthesis of thiazoles and imidazo[2,1-b]thiazoles with various attractive features like being catalyst free, eco-efficient and possessing cost effectiveness, short reaction time, excellent yields and sustainability to fulfill the parameters of green chemistry.

Green approach: An efficient synthesis of 2,4-disubstituted-1,3-thiazoles and selenazoles in aqueous medium under ultrasonic irradiation

An efficient and rapid procedure for the synthesis of 2,4-disubstituted-1,3-thiazoles and selenazoles has been described by the reaction of α-bromoketones with thiourea, phenylthiourea and selenourea at ambient temperature in aqueous medium under ultrasonic irradiation. Analytically pure products were formed within 10-60 s in excellent yields. The advantageous features of this non-conventional methodology over conventional methods are the operational simplicity, easy handling, yield-enhancing, time-reducing, mild reaction conditions and no by-product production.

Effect of substituents on the regioselectivity of the reaction of α-tosyloxyketones with thioureas in acidic medium: Access to 2-aminothiazoles and 2-imino-2,3-dihydrothiazoles

Regioselective condensation of α-tosyloxyacetophenones 1 and N-substituted thioureas 2 in acidic medium to give regioisomers 2-aminothiazoles I and 2-imino-2,3-dihydrothiazoles II is largely influenced by the substituents present on 1 and 2. A mechanism,

Lipase and deep eutectic mixture catalyzed efficient synthesis of thiazoles in water at room temperature

Lipase bio-catalyst or ammonium based deep eutectic mixture efficiently catalyzed aqueous phase synthesis of methyl-thiazole and amino-thiazole derivatives. The simple ammonium deep eutectic catalyst, easily synthesized from choline chloride and urea, is inexpensive, recyclable and bio-degradable, making it suitable for industrial applications. Springer Science+Business Media, LLC 2012.

A library of novel allosteric inhibitors against fructose 1,6-bisphosphatase

The identification of a proper lead compound for fructose 1,6-bisphosphatase (FBPase) is a critical step in the process of developing novel therapeutics against type-2 diabetes. Herein, we have successfully generated a library of allosteric inhibitors against FBPase as potential anti-diabetic drugs, of which, the lead compound 1b was identified through utilizing a virtual high-throughput screening (vHTS) system, which we have developed. The thiazole-based core structure was synthesized via the condensation of α-bromo-ketones with thioureas and substituents on the two aryl rings were varied. 4c was found to inhibit pig kidney FBPase approximately fivefold better than 1b. In addition, we have also identified 10b, a tight binding fragment, which can be use for fragment-based drug design purposes.

Aqueous NaHSO4 catalyzed regioselective and versatile synthesis of 2-thiazolamines

The green acidic catalyst NaHSO4 was used for the synthesis of some novel substituted 2-thiazolamines in water under mild conditions in high regioselectivity.

The Hantzsch Thiazole Synthesis under Acidic Conditions: Change of Regioselectivity

The condensation of α-halogeno ketones with N-monosubstituted thioureas in neutral solvent leads exclusively to 2-(N-substituted amino)thiazoles.In the present work it was shown that under acidic conditions mixtures of 2-(N-substituted amino)thiazoles and 3-substituted 2-imino-2,3-dihydrothiazoles are formed. (The isomers were distinguished by characteristic differences between their 5-H 1H n.m.r. signals and the i.r.CO bands of their trifluoroacetate derivatives.) The proportions of the 2-imino-2,3-dihydrothiazoles in the mixtures are influenced by experimental features and by the structures of the starting materials.Reactions in 10 M-HCl-EtOH (1:2) at 80 deg C for 20 min were found to be the most efficient for generating 2-imino-2,3-dihydrothiazoles; in the most favourable case 2-imino-3,4-dimethyl-2,3-dihydrothiazole was obtained in 73 percent yield.A possible explanation of the results is discussed.