TMSCI Promoted Direct sp3 C-H Alkenylation to Construct （E）-2-Styryl-tetrahydrobenzo[d]thiazoles

A high-efficient and stereo-specific approach for the preparation of biologically important （E）-2-styryl-tetra- hydrobenzo[d]thiazoles has been developed via TMSC1 promoted direct sp3 C-H alkenylation of 2-methyl-5,6-di- hydrobenzo[d]thiazol-7（4H）-one under metal-free conditions. Seventeen target co...

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Bibliographic Details
Published in中国化学：英文版 no. 9; pp. 1077 - 1083
Main Author Chengqiao CaO Wenbin Wang Fan Zhang Nianyu Huang Kun Zou
Format Journal Article
LanguageEnglish
Published 2015
Subjects
sp3
X射线衍射分析
三甲基氯硅烷
噻唑
官能团转化
烯基化反应
生物制备
苯乙烯
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Summary:A high-efficient and stereo-specific approach for the preparation of biologically important （E）-2-styryl-tetra- hydrobenzo[d]thiazoles has been developed via TMSC1 promoted direct sp3 C-H alkenylation of 2-methyl-5,6-di- hydrobenzo[d]thiazol-7（4H）-one under metal-free conditions. Seventeen target compounds were synthesized in ex- cellent yields of 82%--98% under the optimal conditions of 300 mol% TMSCI at 110℃ for 2 h, and their chemical structures were elucidated by IR, NMR, ESI-MS, elemental analyses and X-ray crystallography analysis. A plausible mechanism was also proposed, and this method provided a good functional group conversion for the sp3 C-H substrates.
Bibliography:（E）-2-styryl-tetrahydrobenzo[d]thiazole, sp3 C-H alkenylation, TMSCI, synthesis
A high-efficient and stereo-specific approach for the preparation of biologically important （E）-2-styryl-tetra- hydrobenzo[d]thiazoles has been developed via TMSC1 promoted direct sp3 C-H alkenylation of 2-methyl-5,6-di- hydrobenzo[d]thiazol-7（4H）-one under metal-free conditions. Seventeen target compounds were synthesized in ex- cellent yields of 82%--98% under the optimal conditions of 300 mol% TMSCI at 110℃ for 2 h, and their chemical structures were elucidated by IR, NMR, ESI-MS, elemental analyses and X-ray crystallography analysis. A plausible mechanism was also proposed, and this method provided a good functional group conversion for the sp3 C-H substrates.
31-1547/O6
ISSN:1001-604X
1614-7065