TBAB-mediated radical 6-endo-trig ortho-cyclization of N-aryl-N-(prop-2-yn-1-yl)benzenesulfonamide for the synthesis of 3-bromo-1,2-dihydroquinoline |
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| Authors: | Min Yang Xin Hu Banlai Ouyang Wenlin Xie Jin-Biao Liu |
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| Affiliation: | 1. Department of Forensic Science, Gannan Medical University, 1 Yixueyuan Road, Ganzhou, Jiangxi 341000, China;2. Department of Chemistry, Nanchang Normal University, Nanchang 330032, China;3. School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Hunan 411201, China;4. Department of Chemistry, Jiangxi University of Science and Technology, 86 Hongqi Road, Ganzhou 341000, China |
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| Abstract: | In this work, we described a new synthetic route of 3-bromo-1,2-dihydroquinoline derivatives based on the TBAB/Oxone-mediated radical 6-endo-trig ortho-cyclization of 2-alkynylbenzamide. The reaction proceeded smoothly with moderate functional group tolerance and high reaction efficiency. It is believed that radical addition, 6-endo-dig cyclization, and oxidation are all involved in the reaction processes. Furthermore, we successfully demonstrated the usability of these derivatives in further functionalization. |
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| Keywords: | Corresponding author. 3-Bromo-1,2-dihydroquinoline Radical addition |
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