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

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...

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Autores principales: Sa, Yun, Cai, Mao-Xin, Lv, Xin, Wu, Ai-Bin, Shu, Wen-Ming, Yu, Wei-Chu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9677437/
https://www.ncbi.nlm.nih.gov/pubmed/36425163
http://dx.doi.org/10.1039/d2ra06523a
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author Sa, Yun
Cai, Mao-Xin
Lv, Xin
Wu, Ai-Bin
Shu, Wen-Ming
Yu, Wei-Chu
author_facet Sa, Yun
Cai, Mao-Xin
Lv, Xin
Wu, Ai-Bin
Shu, Wen-Ming
Yu, Wei-Chu
author_sort Sa, Yun
collection PubMed
description 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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spelling pubmed-96774372022-11-23 Intramolecular redox cyclization reaction access to cinnolines from 2-nitrobenzyl alcohol and benzylamine via intermediate 2-nitrosobenzaldehyde Sa, Yun Cai, Mao-Xin Lv, Xin Wu, Ai-Bin Shu, Wen-Ming Yu, Wei-Chu RSC Adv Chemistry 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. The Royal Society of Chemistry 2022-11-21 /pmc/articles/PMC9677437/ /pubmed/36425163 http://dx.doi.org/10.1039/d2ra06523a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Sa, Yun
Cai, Mao-Xin
Lv, Xin
Wu, Ai-Bin
Shu, Wen-Ming
Yu, Wei-Chu
Intramolecular redox cyclization reaction access to cinnolines from 2-nitrobenzyl alcohol and benzylamine via intermediate 2-nitrosobenzaldehyde
title Intramolecular redox cyclization reaction access to cinnolines from 2-nitrobenzyl alcohol and benzylamine via intermediate 2-nitrosobenzaldehyde
title_full Intramolecular redox cyclization reaction access to cinnolines from 2-nitrobenzyl alcohol and benzylamine via intermediate 2-nitrosobenzaldehyde
title_fullStr Intramolecular redox cyclization reaction access to cinnolines from 2-nitrobenzyl alcohol and benzylamine via intermediate 2-nitrosobenzaldehyde
title_full_unstemmed Intramolecular redox cyclization reaction access to cinnolines from 2-nitrobenzyl alcohol and benzylamine via intermediate 2-nitrosobenzaldehyde
title_short Intramolecular redox cyclization reaction access to cinnolines from 2-nitrobenzyl alcohol and benzylamine via intermediate 2-nitrosobenzaldehyde
title_sort intramolecular redox cyclization reaction access to cinnolines from 2-nitrobenzyl alcohol and benzylamine via intermediate 2-nitrosobenzaldehyde
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9677437/
https://www.ncbi.nlm.nih.gov/pubmed/36425163
http://dx.doi.org/10.1039/d2ra06523a
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AT yuweichu intramolecularredoxcyclizationreactionaccesstocinnolinesfrom2nitrobenzylalcoholandbenzylamineviaintermediate2nitrosobenzaldehyde

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