控制螺环环氧吲哚开环的区域选择性以高效合成 C(3)-N(1')-双吲哚和 C(3)-N(1')-二吲哚基甲烷。
Controlling the regioselectivity of the ring opening of spiro-epoxyoxindoles for efficient synthesis of C(3)-N(1')-bisindoles and C(3)-N(1')-diindolylmethane.
机构信息
Centre of Biomedical Research, Sanjay Gandhi Post-Graduate Institute of Medical Sciences Campus, Raebareli Road, Lucknow 226014, India.
Dept. of Chemical Sciences, Indian Institute of Science Education and Research Mohali, Manauli PO 140306, Punjab, India.
出版信息
Org Biomol Chem. 2019 Sep 7;17(33):7747-7759. doi: 10.1039/c9ob01249d. Epub 2019 Aug 6.
An efficient strategy for the construction of both C(3)-N(1') bisindoles and C(3)-N(1') diindolylmethane has been explored via proper tuning of the nucleophilicity of indoline/indole to spiro-epoxyoxindole. Lewis acid-catalyzed highly regio- as well as chemoselective coupling at the C-3 centre of spiro-epoxyoxindoles with indolines furnishes C(3)-N(1') bisindoles whereas base mediated and Lewis acid-catalyzed regioselective coupling at the less hindered site of spiro-epoyoxindoles with indoles via the S2 mechanism provides C(3)-N(1') diindolylmethane.
通过适当调节吲哚啉/吲哚的亲核性，探索了一种构建 C(3)-N(1') 双吲哚和 C(3)-N(1') 二吲哚甲烷的有效策略。路易斯酸催化的 spiro-环氧吲哚与吲哚啉在 C-3 中心的高区域和化学选择性偶联，生成 C(3)-N(1') 双吲哚，而碱介导和路易斯酸催化的通过 S2 机制在 spiro-环氧吲哚的非位阻位点与吲哚的区域选择性偶联提供了 C(3)-N(1') 二吲哚甲烷。
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