Synthesis of 3-substituted 8,9-didehydroazepino[4,5-b]indolines via ring expansion reaction of pyrroloindolines |
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| Authors: | Fu-Sheng Wang Dan ZhangChen Kong Yong Qin |
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| Institution: | a Key Laboratory of Drug Targeting and Novel Delivery System of the Ministry of Education, West China School of Pharmacy, Sichuan University, Chengdu 610041, Sichuan Province, PR China
b College of Pharmacy, Dali University, Dali 671000, Yunnan Province, PR China |
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| Abstract: | An unexpected ring expansion reaction was observed to give the 3-substituted 8,9-didehydroazepinoindolines when 3-substituted pyrroloindolines reacted with electron-deficient acetylenes in the presence of catalytic amount of CuI. The ring expansion reaction proceeded via a three-step one-pot cascade pathway of aza-Michael-addition/ring-opening/iminium-cyclization. |
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| Keywords: | 3-Substituted didehydroazepinoindoline Copper catalysis Michael addition Imimium cyclization Ring expansion |
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