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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| Published in | 中国化学：英文版 no. 9; pp. 1077 - 1083 |
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| Main Author | |
| Format | Journal Article |
| Language | English |
| Published |
2015
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| Subjects | |
| Online Access | Get full text |
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| Abstract | 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. |
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| AbstractList | 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. |
| Author | Chengqiao CaO Wenbin Wang Fan Zhang Nianyu Huang Kun Zou |
| AuthorAffiliation | Hubei Key Laboratory of Natural Products Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang, Hubei 443002, China |
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| Notes | （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 |
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| Snippet | A high-efficient and stereo-specific approach for the preparation of biologically important （E）-2-styryl-tetra- hydrobenzo[d]thiazoles has been developed via... |
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| SubjectTerms | 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 |
| Title | TMSCI Promoted Direct sp3 C-H Alkenylation to Construct （E）-2-Styryl-tetrahydrobenzo[d]thiazoles |
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