Issue 7, 2024

Synthesis of the dibenzo[b,d]azepine skeleton via a catalyst-free ring expansion domino reaction

Abstract

In this article, a hitherto unreported catalyst-free ring expansion reaction of tetrahydroisoquinolines with o-alkynylarylaldehydes for the construction of the dibenzo[b,d]azepine skeleton is described. Using air as a “green” oxidant, some important biologically active dibenzo[b,d]azepines were produced with favorable functional group tolerance and a wide substrate scope. The synthetic potential was further confirmed by facile scale-up reactions and the synthesis of isoindoline derivatives.

Graphical abstract: Synthesis of the dibenzo[b,d]azepine skeleton via a catalyst-free ring expansion domino reaction

Supplementary files

Article information

Article type
Paper
Submitted
27 noy 2023
Accepted
20 fev 2024
First published
21 fev 2024

Green Chem., 2024,26, 3786-3790

Synthesis of the dibenzo[b,d]azepine skeleton via a catalyst-free ring expansion domino reaction

T. Guo, P. Hu, J. Li, Y. Zhou, P. Zhang, Y. Zhao and C. Zhu, Green Chem., 2024, 26, 3786 DOI: 10.1039/D3GC04626E

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