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

ABSTRACT: 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.

SUBMITTER: Chen PY

PROVIDER: S-EPMC8694891 | biostudies-literature | 2021 Feb

REPOSITORIES: biostudies-literature

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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 PY Hsu Chi-Wei CW Ho Tong-Ing TI Ho Jinn-Hsuan JH

RSC advances 20210210 12

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 mechan ...[more]

PMID: 35423196

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