NBS-mediated sequential one-pot synthesis of multifunctionalized thiazoles and thiophenes from 1,3-dicarbonyl compounds and mercaptonitrile salts |
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| Authors: | Laichun Luo Lanlan MengQi Sun Zemei Ge Runtao Li |
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| Affiliation: | State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, 38 Xueyuan Road, Haidian District, Beijing 100191, PR China |
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| Abstract: | A NBS-mediated sequential one-pot synthesis of multifunctionalized thiazoles and thiophenes from 1,3-dicarbonyl compounds and mercaptonitrile salts has been developed under mild conditions. This transformation involves sequential bromination/SN2 alkylation/Thorpe–Ziegler cyclization/regio-selective elimination of a –COR group, affording the desired products in moderate to good yields. The sequence of the leaving reactivity of –COR groups was determined and a possible mechanism was proposed. |
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| Keywords: | Multifunctionalized thiazoles and thiophenes Sequential one-pot synthesis Thorpe&ndash Ziegler cyclization 1,3-Dicarbonyl compounds NBS |
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