Cu(II)-Catalyzed Cascade of N-Phenyl-o-phenylenediamine with Benzaldehyde: One-Step Direct Construction of 2-(1-Phenyl-1H-benzo[d]imidazol-2-yl)phenols.

doi:10.1021/acs.joc.3c00733

Paper

Cu(II)-Catalyzed Cascade of N-Phenyl-o-phenylenediamine with Benzaldehyde: One-Step Direct Construction of 2-(1-Phenyl-1H-benzo[d]imidazol-2-yl)phenols.

Published Jun 1, 2023 · Jingpeng Li, Zhuoyu Wang, Guiyun Zeng

The Journal of organic chemistry

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Abstract

A practical protocol for the construction of hydroxylated 2-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenols (PBIs) from N-phenyl-o-phenylenediamine with benzaldehydes was developed. The cascade reaction was enabled by heating a mixture of the two substrates in the presence of air as an oxidant and anhydrous Cu(OAc)2 as a catalyst in dimethyl sulfoxide, and a diverse series of PBIs were synthesized in moderate to good yields (69-81%). Furthermore, the synthesis of the PBIs was enabled via a one-pot cascade reaction that proceeded through subsequent dehydration condensation, intramolecular cyclization, and aromatic C-H hydroxylation. This protocol can be used for the synthesis of hydroxylated PBI via a one-pot annulation C-H hydroxylation reaction rather than through a series of multistep reactions, which provides the possibility of further modification.

Study Snapshot

This study developed a one-pot protocol for synthesizing hydroxylated 2-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenols from N-phenyl-o-phenylenediamine and benzaldehydes, enabling

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Cu(II)-Catalyzed Cascade of N-Phenyl-o-phenylenediamine with Benzaldehyde: One-Step Direct Construction of 2-(1-Phenyl-1H-benzo[d]imidazol-2-yl)phenols.

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Citations

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Cuminaldehyde-derived benzimidazole metal complexes show potential as photocatalysts and antimicrobial and biofilm inhibitors, with the mixed ligand copper complex showing the highest antimicrobial and biofilm activities.

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Microwave-assisted four-component cascade reaction allows for the rapid, metal-free synthesis of fully substituted pyrroles in moderate to excellent yields in 3 minutes.