Issue 17, 2022

One-step synthesis of azepino[3,4-b]indoles by cooperative aza-[4 + 3] cycloaddition from readily available feedstocks

Abstract

Azepino[3,4-b]indoles are a family of molecules with pharmaceutical significance that contain an aza-seven-membered ring system. However, synthetic approaches to this scaffold are limited and typically require multiple steps. Here, we demonstrate the feasibility of obtaining azepino[3,4-b]indoles by one-step synthesis from a four-component reaction system comprising readily available starting materials, i.e., an amino acid, an indole, and an aniline. This transformation affords a diverse range of azepino[3,4-b]indoles in a highly efficient manner. We propose that the self-sorting integration of two kinetically unstable intermediates, an indol-3-yl cation and an N-arylimine, is key to realizing the cooperative aza-[4 + 3] cycloaddition.

Graphical abstract: One-step synthesis of azepino[3,4-b]indoles by cooperative aza-[4 + 3] cycloaddition from readily available feedstocks

Supplementary files

Article information

Article type
Research Article
Submitted
01 Jun 2022
Accepted
10 Jul 2022
First published
12 Jul 2022

Org. Chem. Front., 2022,9, 4640-4648

One-step synthesis of azepino[3,4-b]indoles by cooperative aza-[4 + 3] cycloaddition from readily available feedstocks

J. Ma, T. Chen, X. Chen, Y. Zhou, Z. Yu, S. Zhuang, M. Alimu, Y. Wu, J. Xiang and A. Wu, Org. Chem. Front., 2022, 9, 4640 DOI: 10.1039/D2QO00816E

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