2521-25-7Relevant 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.
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.
Discovery of amide replacements that improve activity and metabolic stability of a bis-amide smoothened antagonist hit
Brown, Matthew L.,Aaron, Wade,Austin, Richard J.,Chong, Angela,Huang, Tom,Jiang, Ben,Kaizerman, Jacob A.,Lee, Gary,Lucas, Brian S.,McMinn, Dustin L.,Orf, Jessica,Rong, Minqing,Toteva, Maria M.,Xu, Guifen,Ye, Qiuping,Zhong, Wendy,Degraffenreid, Michael R.,Wickramasinghe, Dineli,Powers, Jay P.,Hungate, Randall,Johnson, Michael G.
scheme or table, p. 5206 - 5209 (2011/10/09)
A bis-amide antagonist of Smoothened, a seven-transmembrane receptor in the Hedgehog signaling pathway, was discovered via high throughput screening. In vitro and in vivo experiments demonstrated that the bis-amide was susceptible to N-acyl transferase mediated amide scission. Several bioisosteric replacements of the labile amide that maintained in vitro potency were identified and shown to be metabolically stable in vitro and in vivo.
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.
An efficient, catalyst- and solvent-free synthesis of imidazo[1,2-a] pyridines and 2,4-disubstituted thiazoles on grinding
Zhu, Dongjian,Chen, Jiuxi,Wu, Dengze,Liu, Miaochang,Ding, Jinchang,Wu, Huayue
experimental part, p. 84 - 86 (2009/10/15)
An efficient synthesis of imidazo[1,2-a]pyridines and 2,4-disubstituted thiazoles in excellent yield under catalyst-and solvent-free conditions at room temperature on grinding has been developed. The important features of this method are that it is reasonably fast, very clean, high yielding, simple workup and environmentally benign.
Efficient and expeditious synthesis of di- and trisubstituted thiazoles in PEG under catalyst-free conditions
Zhu, Dongjian,Chen, Jiuxi,Xiao, Huilong,Liu, Miaochang,Ding, Jinchang,Wu, Huayue
experimental part, p. 2895 - 2906 (2009/12/03)
An efficient and expeditious catalyst-free protocol was developed for the construction of di- and trisubstituted thiazoles from -haloketones and thioureas/thioamides in PEG. The reaction was carried out at ambient temperature, and the products were obtained in excellent isolated yields (91-98%). Additionally, PEG could be recovered easily and was reused without evident loss in activity.
A comparative study on stille cross-coupling reactions of 2-phenylthiazoles and 2-phenyloxazoles
Haemmerle, Johanna,Spina, Markus,Schnuerch, Michael,Mihovilovic, Marko D.,Stanetty, Peter
experimental part, p. 3099 - 3107 (2009/04/06)
A systematic study of the cross-coupling capability of the 4- and 5-positions of 2-phenylthiazoles and -oxazoles under Stille conditions is presented. The azoles were both applied as stannanes and as the halide component. The obtained results were compared regarding the position of the halide and Bu3Sn group. In order to establish a general reactivity platform for those heterocyclic systems, a broad variety of aromatic and heteroaromatic halides were coupled and some significant differences concerning the coupling properties of the investigated systems were observed. Georg Thieme Verlag Stuttgart.
Liquid-phase organic synthesis of thiazoles using poly(ethylene glycol)-bound sulfonyl chloride resin
Liu, Xiao-Ling,Wang, Qiu-Ying,Sheng, Shou-Ri,Xu, Chen,Cai, Ming-Zhong
, p. 3338 - 3345 (2008/12/22)
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.
Benzene compounds
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Page/Page column 77, (2010/11/27)
The present invention provides novel benzene compounds presented by the following formulas, and analogs thereof, that exert an ACC activity-inhibiting effect that is effective in the treatment of obesity, hyperlipemia, fatty liver, hyperglycemia, impaired glucose tolerance, diabetes, diabetic complications (diabetic peripheral neuropathy, diabetic nephropathy, diabetic retinopathy, and diabetic macroangiopathy, hypertension, arteriosclerosis), hypertension, and arteriosclerosis.
Comparing the reactivity of the 4- and 5-positions of 2-phenylthiazoles in stille cross-coupling reactions
H?mmerle, Johanna,Schnürch, Michael,Stanetty, Peter
, p. 2975 - 2978 (2008/03/12)
A systematic study of the cross-coupling capability of 4-and 5-substituted 2-phenylthiazoles under Stille conditions is presented. Two cross-coupling options were investigated: 1) combination of thiazolylstannanes with various aryl(hetaryl) halides and, 2) reaction of halothiazoles with PhSn(Bu) 3 as coupling partner. The results obtained from the cross-coupling reactions on the 4- and 5-positions of the thiazole system were compared regarding the influence of the position of the halide (Br, I) and the Bu 3Sn group on both coupling partners. A broad selection of aromatic and heteroaromatic halides was coupled in order to establish a general reactivity platform for this heterocyclic system. Georg Thieme Verlag Stuttgart.
