Synthesis of 6‐Alkylidene‐5,6‐dihydro‐4H‐1,3‐thiazine Derivatives via the Cyclization of N‐3‐Bromo‐3‐alkenylthioamides |
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| Authors: | Shusu Shen Yu Liu |
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| Institution: | 1. Center for Separation and Purification Materials & Technologies, Suzhou University of Science and Technology, Suzhou, Jiangsu 215009, China;2. Institute of Functional Nano & Soft Materials (FUNSOM), Jiangsu Key Laboratory for Carbon‐Based Functional Materials & Devices, Soochow University, Suzhou, Jiangsu 215123, China |
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| Abstract: | By the treatment of N‐3‐bromo‐3‐alkenylthioamides with sodium hydroxide in DMF‐H2O in the presence of tetra‐butylammonium bromide, series of 6‐alkylidene‐5,6‐dihydro‐4H‐1,3‐thiazine derivatives were prepared in moderate to good yields. The cyclization is supposed to proceed via both the intramolecular vinylic nucleophilic substitution and the elimination‐addition mechanisms (formation of acetylenic intermediates) in a competitive manner. |
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| Keywords: | 5 6‐dihydro‐4H‐1 3‐thiazine derivatives N‐3‐bromo‐3‐alkenylthioamides intramolecular vinylic nucleophilic substitution elimination/addition |
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