15087-97-5

Upstream product

• 70-11-1 α-bromoacetophenone 
• 621-83-0 N-benzylthiourea 
• 98-86-2 acetophenone 
• 2010-06-2 2-Amino-4-phenylthiazole 
• 100-51-6 benzyl alcohol 
• 2290-65-5 trimethylsilyl isothiocyanate 
• 100-46-9 benzylamine 
• 88333-03-3 Benzyl isocyanide 
• 1260001-52-2 1,2-bis[(2-phenyl-1,3-dioxolan-2-yl)methyl]disulfane 
• 100-42-5 styrene 
• 621-83-0 N-(benzyl)carbamimidothioic acid 
• 100-39-0 benzyl bromide 
• 19433-17-1 acetophenone O-acetyloxime 
• 622-78-6 Benzyl isothiocyanate 

Relevant academic research and scientific papers

Efficient synthesis of 2,4-disubstituted thiazoles using ionic liquid?under ambient conditions: a practical approach towards?the?synthesis of Fanetizole

A highly efficient and rapid synthesis of 2-amino-4-arylthiazoles and 2-methyl-4-arylthiazole from α-bromoketone and thiourea/thioamide is described using room temperature ionic liquid at ambient conditions. The method is simple, rapid and practical, generating thiazole derivatives in excellent isolated yields. This protocol is utilized for a commercially feasible synthesis of an anti-inflammatory agent, Fanetizole.

One-pot synthesis of 4-aryl-2-aminothiazoles from styrenes and thioureas promoted by tribromoisocyanuric acid

A simple and efficient one-pot protocol has been developed for the conversion of styrenes into 4-aryl-2-aminothiazoles using readily available starting materials. Tribromoisocyanuric acid was successfully used for the co-bromination and oxidation of styrenes to give phenacyl bromides, which in the presence of thioureas produced the corresponding 4-aryl-2-aminothiazoles in 48–70% yield. The protocol involves three reactions in one process: a tandem (formation of phenacyl bromides from styrenes) followed by a telescoped (conversion to thiazole) reaction.

Structure-Based Design of N-(5-Phenylthiazol-2-yl)acrylamides as Novel and Potent Glutathione S-Transferase Omega 1 Inhibitors

Using reported glutathione S-transferase omega 1 (GSTO1-1) cocrystal structures, we designed and synthesized acrylamide-containing compounds that covalently bind to Cys32 on the catalytic site. Starting from a thiazole derivative 10 (GSTO1-1 IC50 = 0.6 μM), compound 18 was synthesized and cocrystallized with GSTO1. Modification on the amide moiety of hit compound 10 significantly increased the GSTO1-1 inhibitory potency. We solved the cocrystal structures of new derivatives, 37 and 44, bearing an amide side chain bound to GSTO1. These new structures showed a reorientation of the phenyl thiazole core of inhibitors, 37 and 44, when compared to 18. Guided by the cocrystal structure of GSTO1:44, analogue 49 was designed, resulting in the most potent GSTO1-1 inhibitor (IC50 = 0.22 ± 0.02 nM) known to date. We believe that our data will form the basis for future studies of developing GSTO1-1 as a new drug target for cancer therapy.

In Situ Activation of Disulfides for Multicomponent Reactions with Isocyanides and a Broad Range of Nucleophiles

Activation of disulfides with N-halogen succinimide in the presence of TEMPO allows insertion reaction by an isocyanide, the product of which can further accept a wide range of nucleophiles for the generation of isothioureas and related molecular moieties. This new procedure overcomes previous methods that accept essentially only aryl amines as the third nucleophilic component. The diverse nucleophiles usable in our new protocol make this approach a general method for de novo synthesis of many S-containing heterocycles.

Highly efficient heterogeneous copper-catalysed coupling of oxime acetates with isothiocyanates leading to 2-aminothiazoles

The heterogeneous coupling reaction of oxime acetates with isothiocyanates was achieved at 110°C in toluene in air in the presence of a bidentate nitrogen-functionalised MCM-41-immobilised copper(I) complex (MCM-41-2N-CuI) with Cs2CO3 as base to afford a variety of 2-aminothiazoles in good yields. The MCM-41-2N-CuI catalyst can be easily recovered by a simple filtration and reused at least eight times without significant loss of activity.

Efficient and practical catalyst-free-like dehydrative N-alkylation of amines and sulfinamides with alcohols initiated by aerobic oxidation of alcohols under air

We developed simple and practical N-alkylation reactions of amines and sulfinamides with primary and secondary alcohols by using only catalytic amounts of air as the initiator without adding any external catalysts. This method has advantages of simple conditions, easy operation, and comparatively wider scope of substrates, providing an efficient and green catalyst-free-like alcohol-based dehydrative N-alkylation method. Mechanistic studies revealed that air initiated the reactions by aerobic oxidation of the alcohols to the key initiating aldehydes or ketones in the presence of bases.

Copper-Catalyzed Coupling of Oxime Acetates with Isothiocyanates: A Strategy for 2-Aminothiazoles

A new strategy for 2-aminothiazoles is developed via the copper-catalyzed coupling of oxime acetates with isothiocyanates. Various 4-substituted and 4,5-disubstituted 2-aminothiazoles were formed smoothly under mild reaction conditions. This process involved copper-catalyzed N-O bond cleavage, activation of vinyl sp2 C-H bonds, and C-S/C-N bond formations. It is noteworthy that the oxime acetates were used not only as a substrate but also as a single oxidant.

Carbon tetrabromide mediated oxidative cyclocondensation of ketones and thioureas: An easy access to 2-aminothiazoles

A simple, mild, and efficient one-pot method for the synthesis of substituted 2-aminothiazoles has been reported. The reaction involves the formation of sulfenyl bromide as an umpolung intermediate of nucleophilic sulfur, which is responsible for C-S bond formation leading to oxidative cyclization of ketones and thioureas to furnish the desired products. Carbon tetrabromide was used as a convenient and mild brominating reagent under basic condition at room temperature to give 2-aminothiazoles in good to excellent yields.

A simple, three-component synthesis of 2-aminothiazoles using trimethylsilyl isothiocyanate

The first multicomponent, solution-phase protocol to prepare privileged 2-aminothiazoles from α-bromocarbonyl compounds and amines (aromatic and aliphatic) using commercially available trimethylsilyl isothiocyanate is described.

Sodium hydroxide catalyzed N-alkylation of (hetero) aromatic primary amines and N1,C5-dialkylation of 4-phenyl-2-aminothiazoles with benzyl alcohols

In the presence of a catalytic amount of NaOH, the selective N-alkylation of various heteroaromatic primary amines is reported. With 1 equiv of NaOH, N1,C5-dialkylation of 4-phenyl-2-aminothiazoles has been investigated. Reaction of in situ generated aldehyde with amine yields the N-alkylated and N1,C5-dialkylated products through hydride ion transformation from alcohol.