Issue 19, 2022

Brønsted acid-catalyzed cascade cyclization: an efficient strategy for divergent synthesis of cyclohepta[b]indole derivatives

Abstract

An efficient acid-catalyzed three-component cascade strategy was established on the basis of a crucial conversion of BIMs to vinylindoles to synthesize a privileged scaffold, phenyl-substituted dihydrocyclohepta[b]indole carboxylate. The vinylindole intermediates worked as 1,4-bisnucleophiles and could be trapped by atropaldehyde acetals to construct diphenyl-substituted dihydrocyclohepta[b]indoles. A [5 + 2] cyclization of 2-aryl-3,4-dihydropyrans with 2,3-unsubstituted indoles was also established, which provided another route to access tetrahydrocyclohepta[b]indoles. Readily available materials, inexpensive metal-free catalysts, eco-friendly solvents and divergent synthesis ensured these methods are practically attractive.

Graphical abstract: Brønsted acid-catalyzed cascade cyclization: an efficient strategy for divergent synthesis of cyclohepta[b]indole derivatives

Supplementary files

Article information

Article type
Communication
Submitted
01 Jun 2022
Accepted
08 Sep 2022
First published
11 Sep 2022

Green Chem., 2022,24, 7376-7381

Brønsted acid-catalyzed cascade cyclization: an efficient strategy for divergent synthesis of cyclohepta[b]indole derivatives

S. Chen, Z. Chen, T. Zhang, B. Zhao, B. You, M. Li and Y. Gu, Green Chem., 2022, 24, 7376 DOI: 10.1039/D2GC02072F

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