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

作　　者：Chengqiao CaO Wenbin Wang Fan Zhang Nianyu Huang Kun Zou 

机构地区：[1]Hubei Key Laboratory of Natural Products Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang, Hubei 443002, China

出　　处：《Chinese Journal of Chemistry》2015年第9期1077-1083,共7页中国化学（英文版）

基　　金：The authors thank the finance supported by the National Natural Science Foundation of China （No. 21272136）, and Scientific Research Innovation Founda- tion of Graduate School of China Three Gorges Univer- sity.

摘　　要：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.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.

关 键 词：（E）-2-styryl-tetrahydrobenzo[d]thiazole sp3 C-H alkenylation TMSCI synthesis 

分 类 号：TQ252.5[化学工程—有机化工] TP316.7[自动化与计算机技术—计算机软件与理论]