Reported herein are the chemodivergent (4 + 3) cycloadditions of 2-indolylmethanols with 1,3,5-triazinanes. As opposed to the previous (3 + n) cycloadditions of 2-indolylmethanols as three-atom synthons, this divergent protocol employs 2-indolylmethanols as platform four-atom synthons by using the OH group as a nucleophilic group. The gem-diaryl effect enables divergent regioselectivity. Primary 2-indolylmethanols display N1-nuleophilicity, while tertiary diaryl 2-indolylmethanols exhibit C3-nucleophilicity. As such, various polycyclic indoles, oxadiazepino[5,6-a]indoles and oxazepino[6,5-b]indoles, have been collectively prepared in good yields.

中文翻译：

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2-吲哚甲醇与 1,3,5-三嗪的化学发散 (4 + 3) 环加成：获得多环吲哚

本文报道了2-吲哚基甲醇与1,3,5-三嗪的化学发散(4+3)环加成。与之前将 2-吲哚甲醇作为三原子合成子的 (3 + n ) 环加成相反，该不同方案通过使用 OH 基团作为亲核基团，采用 2-吲哚甲醇作为平台四原子合成子。宝石二芳基效应能够实现不同的区域选择性。伯2-吲哚甲醇表现出N1-亲核性，而叔二芳基2-吲哚甲醇表现出C3-亲核性。因此，各种多环吲哚、氧杂氮杂[5,6- a ]吲哚和氧杂氮杂[6,5- b ]吲哚已以良好的产率共同制备。