The selective synthesis of N-arylbenzene-1,2-diamines or 1-arylbenzimidazoles by irradiating 4-methoxy-4′-substituted-azobenzenes in different solvents

The solvent-controllable photoreaction of 4-methoxyazobenzenes to afford 1-aryl-1H-benzimidazoles or N-arylbenzene-1,2-diamines has been studied. The irradiation of 4-methoxyazobenzenes in DMF containing 0.5 M hydrochloric acid provided N(2)-aryl-4-methoxybenzene-1,2-diamines as the major product, w...

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Autores principales: Chen, Po-Yi, Hsu, Chi-Wei, Ho, Tong-Ing, Ho, Jinn-Hsuan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8694891/
https://www.ncbi.nlm.nih.gov/pubmed/35423196
http://dx.doi.org/10.1039/d0ra10068d
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author Chen, Po-Yi
Hsu, Chi-Wei
Ho, Tong-Ing
Ho, Jinn-Hsuan
author_facet Chen, Po-Yi
Hsu, Chi-Wei
Ho, Tong-Ing
Ho, Jinn-Hsuan
author_sort Chen, Po-Yi
collection PubMed
description The solvent-controllable photoreaction of 4-methoxyazobenzenes to afford 1-aryl-1H-benzimidazoles or N-arylbenzene-1,2-diamines has been studied. The irradiation of 4-methoxyazobenzenes in DMF containing 0.5 M hydrochloric acid provided N(2)-aryl-4-methoxybenzene-1,2-diamines as the major product, while irradiation in acetal containing 0.16 M hydrochloric acid led to 1-aryl-6-methoxy-2-methyl-1H-benzimidazoles as the major product. A possible reaction mechanism explaining the selectivity was also discussed.
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spelling pubmed-86948912022-04-13 The selective synthesis of N-arylbenzene-1,2-diamines or 1-arylbenzimidazoles by irradiating 4-methoxy-4′-substituted-azobenzenes in different solvents Chen, Po-Yi Hsu, Chi-Wei Ho, Tong-Ing Ho, Jinn-Hsuan RSC Adv Chemistry The solvent-controllable photoreaction of 4-methoxyazobenzenes to afford 1-aryl-1H-benzimidazoles or N-arylbenzene-1,2-diamines has been studied. The irradiation of 4-methoxyazobenzenes in DMF containing 0.5 M hydrochloric acid provided N(2)-aryl-4-methoxybenzene-1,2-diamines as the major product, while irradiation in acetal containing 0.16 M hydrochloric acid led to 1-aryl-6-methoxy-2-methyl-1H-benzimidazoles as the major product. A possible reaction mechanism explaining the selectivity was also discussed. The Royal Society of Chemistry 2021-02-10 /pmc/articles/PMC8694891/ /pubmed/35423196 http://dx.doi.org/10.1039/d0ra10068d Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Chen, Po-Yi
Hsu, Chi-Wei
Ho, Tong-Ing
Ho, Jinn-Hsuan
The selective synthesis of N-arylbenzene-1,2-diamines or 1-arylbenzimidazoles by irradiating 4-methoxy-4′-substituted-azobenzenes in different solvents
title The selective synthesis of N-arylbenzene-1,2-diamines or 1-arylbenzimidazoles by irradiating 4-methoxy-4′-substituted-azobenzenes in different solvents
title_full The selective synthesis of N-arylbenzene-1,2-diamines or 1-arylbenzimidazoles by irradiating 4-methoxy-4′-substituted-azobenzenes in different solvents
title_fullStr The selective synthesis of N-arylbenzene-1,2-diamines or 1-arylbenzimidazoles by irradiating 4-methoxy-4′-substituted-azobenzenes in different solvents
title_full_unstemmed The selective synthesis of N-arylbenzene-1,2-diamines or 1-arylbenzimidazoles by irradiating 4-methoxy-4′-substituted-azobenzenes in different solvents
title_short The selective synthesis of N-arylbenzene-1,2-diamines or 1-arylbenzimidazoles by irradiating 4-methoxy-4′-substituted-azobenzenes in different solvents
title_sort selective synthesis of n-arylbenzene-1,2-diamines or 1-arylbenzimidazoles by irradiating 4-methoxy-4′-substituted-azobenzenes in different solvents
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8694891/
https://www.ncbi.nlm.nih.gov/pubmed/35423196
http://dx.doi.org/10.1039/d0ra10068d
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