2362-68-7Relevant academic research and scientific papers
Br?nsted acid-promoted thiazole synthesis under metal-free conditions using sulfur powder as the sulfur source
Ni, Penghui,Tan, Jing,Li, Rong,Huang, Huawen,Zhang, Feng,Deng, Guo-Jun
, p. 3931 - 3935 (2020/02/04)
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.
Visible Light-Induced Difunctionalization of Alkynes: The Synthesis of Thiazoles and 1,1-Dibromo-1-en-3-ynes
Huang, Xiaoying,Chen, Hui,Huang, Zhongzhi,Xu, Yanli,Li, Fangyao,Ma, Xianli,Chen, Yanyan
, p. 15283 - 15293 (2019/12/04)
A visible light-induced cascade cyclization of thioamides with alkynes was developed to synthesize 1,3-thiozoles. The sulfur radical generated from thioamide via the single-electron transfer (SET) pathway was promoted by photocatalysis as a key intermediate in this reaction. When bromoalkynes were used as the substrate, the self-coupling products 1,1-dibromo-1-en-3-ynes were obtained in moderate yields, and an energy transfer pathway for this transformation promoted by visible-light photocatalysis was proposed.
Aryliodoazide synthons: A different approach for diversified synthesis of 2-aminothiazole, 1,3-thiazole, and 1,3-selenazole scaffolds
Majnooni, Sahar,Duffield, Joseph,Price, Jessica,Khosropour, Ahmad Reza,Zali-Boeini, Hassan,Beyzavi, M. Hassan
supporting information, p. 516 - 521 (2019/08/01)
Several straightforward and practical processes have been established for the construction of 2-aminothiazoles, 1,3-thiazoles and 1,3-selenazoles from aryliodoazides. These strategies successfully proceed with a wide spectrum of substituted thioamides and its derivatives producing the resulting five-membered heterocycles obtained in satisfactory yields. The unique features of these protocols are operational simplicity and highly functional group tolerance, which make them convenient and practical routes for the preparation of various libraries of 2-aminothiazoles, 1,3-thiazoles, and 1,3-selenazoles.
Syntheses of biodynamic heterocycles: baker’s yeast-assisted cyclocondensations of organic nucleophiles and phenacyl chlorides
Khillare, Lalit D.,Pratap, Umesh R.,Bhosle, Manisha R.,Dhumal, Sambhaji T.,Bhalerao, Mahendra B.,Mane, Ramrao A.
, p. 4327 - 4337 (2017/07/22)
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.
Exploration and Optimization of an Efficient One-pot Sequential Synthesis of Di/tri-substituted Thiazoles from α-Bromoketones, Thioacids Salt, and Ammonium Acetate
Venkateswararao, Eeda,Jalani, Hitesh B.,Manoj,, Manickam,Jung, Sang-Hun
supporting information, p. 1449 - 1456 (2016/09/24)
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.
Programmed synthesis of arylthiazoles through sequential C-H couplings
Tani, Satoshi,Uehara, Takahiro N.,Yamaguchi, Junichiro,Itami, Kenichiro
, p. 123 - 135 (2014/01/06)
A programmed synthesis of privileged arylthiazoles via sequential C-H couplings catalyzed by palladium or nickel catalysts has been accomplished. This versatile protocol can supply all possible arylthiazole substitution patterns (2-aryl, 4-aryl, 5-aryl, 2
A facile and eco-friendly synthesis of diarylthiazoles and diarylimidazoles in water
Kumar, Dalip,Kumar, N. Maruthi,Patel, Gautam,Gupta, Sudeep,Varma, Rajender S.
experimental part, p. 1983 - 1986 (2011/04/25)
A simple, efficient and high yielding greener protocol for the synthesis of substituted thiazoles and imidazoles is described that utilizes the reaction of readily available α-tosyloxy ketones with variety of thioamides/amidines in water.
Oxidative biaryl coupling of thiophenes and thiazoles with arylboronic acids through palladium catalysis: Otherwise difficult C4-selective C-H arylation enabled by boronic acids
Kirchberg, Sylvia,Tani, Satoshi,Ueda, Kirika,Yamaguchi, Junichiro,Studer, Armido,Itami, Kenichiro
supporting information; experimental part, p. 2387 - 2391 (2011/04/21)
(Chemical Equation Presented) It adds up to 4! Thiophenes and thiazoles can be arylated in the 4- rather than the expected 5-position in a new C-H functionalization reaction (see scheme; TEMPO: 2,2,6,6-tetramethylpiperidine-N- oxyl). The boronic acid proved to be the key to achieving the otherwise difficult C4 selectivity. The method was applied to a concise synthesis of a key pharmacological structure with potential for treatment of Alzheimers disease.
A guideline for the arylation of positions 4 and 5 of thiazole via Pd-catalyzed cross-coupling reactions
H?mmerle, Johanna,Schnürch, Michael,Iqbal, Naseer,Mihovilovic, Marko D.,Stanetty, Peter
experimental part, p. 8051 - 8059 (2010/10/21)
The arylation of thiazoles in 4- and 5-position was investigated in detail. Suzuki-Miyaura and Stille cross-coupling reactions were tested using thiazoles either as halide or organometal species. The obtained results were critically compared to develop he
A systematic study of Suzuki-Miyaura cross-coupling reactions on thiazoleboronic esters in the 4- and 5-position
Schnuerch, Michael,Haemmerle, Johanna,Mihovilovic, Marko D.,Stanetty, Peter
experimental part, p. 837 - 843 (2010/09/18)
A systematic study of the Suzuki-Miyaura cross-coupling reaction of thiazoleboronic esters under microwave conditions is presented. Boronic acid esters were prepared in the 4- and 5-position of the thiazole ring and subsequently cross-coupled with a number of different (hetero)aryl halides. Yields of the coupling process depended on the reactivity of the boronic acid at the particular position in the thiazole system, as hydrolysis and subsequent deboronation was found to be a major side reaction. Georg Thieme Verlag Stuttgart.
