文献类型：期刊文献

英文题名：An Efficient One-pot Synthesis of Aryl-substituted 1-(Thiazol-2-yl)-1H-pyrazole-3-carboxylates via a Hantzsch Synthesis-Knorr Reaction Sequence

作者：Gu, Chunhui[1];Zhai, Jiaojiao[1];Jiang, Jianan[1];Liu, Hongwei[1];Wang, Lei[2];Zhu, Dunru[2];Ji, Yafei[1]

机构：[1]E China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R China;[2]Nanjing Univ Technol, State Key Lab Mat Oriented Chem Engn, Coll Chem & Chem Engn, Nanjing 210009, Jiangsu, Peoples R China

年份：2014

卷号：32

期号：2

起止页码：179

外文期刊名：CHINESE JOURNAL OF CHEMISTRY

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000332004000011)，CCR-EXPANDED(收录号:WOS:000332004000011)】；

基金：The authors are grateful to the National Natural Science Foundation of China (Nos. 21176074 and 21171093) for financial support.

语种：英文

外文关键词：one-pot synthesis; Claisen condensation; Hantzsch synthesis; Knorr reaction; 1-(thiazol-2-yl)pyrazole-3-carboxylates

摘要：The treatment of -bromoalkyl aryl ketones and 2-(propan-2-ylidene)hydrazine carbothioamide afforded 4-aryl-2-(2-(propan-2-ylidene)hydrazinyl)thiazoles via a Hantzsch-thiazole synthesis, which reacted with 4-aryl-2,4-diketoesters via a sequential Knorr-pyrazole reaction to deliver a variety of aryl-substituted ethyl 1-(thiazol-2-yl)-1H-pyrazole-3-carboxylates in a one-pot fashion with moderate to high yields. The key intermediates 4-aryl-2,4-diketoesters, existing as its enolic lithium salt, were synthesized in situ by a high-yield tert-BuOLi-mediated Claisen condensation of alkylphenones and diethyl oxalate. This class of elegant molecule comprises aryl groups on the two different heterocyclic cores, and the configurations of two representative molecules were determined by single crystal X-ray crystallography.