Issue 13, 2024

Chemodivergent (4 + 3) cycloadditions of 2-indolylmethanols with 1,3,5-triazinanes: access to polycyclic indoles

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.

Graphical abstract: Chemodivergent (4 + 3) cycloadditions of 2-indolylmethanols with 1,3,5-triazinanes: access to polycyclic indoles

Supplementary files

Article information

Article type
Research Article
Submitted
21 Apr 2024
Accepted
11 May 2024
First published
13 May 2024

Org. Chem. Front., 2024,11, 3624-3629

Chemodivergent (4 + 3) cycloadditions of 2-indolylmethanols with 1,3,5-triazinanes: access to polycyclic indoles

R. Dong, T. Han, L. Huang and G. Mei, Org. Chem. Front., 2024, 11, 3624 DOI: 10.1039/D4QO00657G

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