Chemodivergent (4 + 3) cycloadditions of 2-indolylmethanols with 1,3,5-triazinanes: access to polycyclic indoles†
Guang-Jian
Mei 
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Abstract
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.
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