Issue 51, 2022, Issue in Progress

Intramolecular redox cyclization reaction access to cinnolines from 2-nitrobenzyl alcohol and benzylamine via intermediate 2-nitrosobenzaldehyde

Abstract

A transition-metal-free intramolecular redox cyclization reaction for the synthesis of cinnolines has been developed from 2-nitrobenzyl alcohol and benzylamine. Mechanistic investigations disclosed the involvement of a key intramolecular redox reaction, followed by condensation, azo isomerization to hydrazone, cyclization, and aromatization to form the desired products. Notably, the formation of intermediate 2-nitrosobenzaldehyde and (E)-2-(2-benzylidenehydrazineyl) benzaldehyde plays an important role in this transformation.

Graphical abstract: Intramolecular redox cyclization reaction access to cinnolines from 2-nitrobenzyl alcohol and benzylamine via intermediate 2-nitrosobenzaldehyde

Supplementary files

Article information

Article type
Paper
Submitted
16 Oct 2022
Accepted
16 Nov 2022
First published
21 Nov 2022
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2022,12, 33260-33263

Intramolecular redox cyclization reaction access to cinnolines from 2-nitrobenzyl alcohol and benzylamine via intermediate 2-nitrosobenzaldehyde

Y. Sa, M. Cai, X. Lv, A. Wu, W. Shu and W. Yu, RSC Adv., 2022, 12, 33260 DOI: 10.1039/D2RA06523A

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