Intramolecular redox cyclization reaction access to cinnolines from 2-nitrobenzyl alcohol and benzylamine via intermediate 2-nitrosobenzaldehyde?
RSC Advances Pub Date: 2022-11-21 DOI: 10.1039/D2RA06523A
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.
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Journal Name：RSC Advances
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CAS no.: 89640-58-4
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