TMSCl Promoted Direct sp3 C‐H Alkenylation to Construct (E)‐2‐Styryl‐tetrahydrobenzo[d]thiazoles |
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Authors: | Chengqiao Cao Wenbin Wang Fan Zhang Nianyu Huang Kun Zou |
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Institution: | 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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Abstract: | A high‐efficient and stereo‐specific approach for the preparation of biologically important (E)‐2‐styryl‐tetrahydrobenzod]thiazoles has been developed via TMSCl promoted direct sp3 C‐H alkenylation of 2‐methyl‐5,6‐dihydrobenzod]thiazol‐7(4H)‐one under metal‐free conditions. Seventeen target compounds were synthesized in excellent yields of 82% –98% under the optimal conditions of 300 mol% TMSCl at 110°C 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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Keywords: | (E)‐2‐styryl‐tetrahydrobenzo[d]thiazole sp3 C‐H alkenylation TMSCl synthesis |
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