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A unique one-pot reaction via C[sbnd]C cleavage from aminomethylene benzimidazoles to access benzimidazolones with wide potentiality

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Identifiers
DOI: 10.1016/j.tetlet.2014.05.113
Keywords
  • Benzimidazole
  • Benzimidazolone
  • C[Sbnd]C Cleavage
  • Synthesis

Abstract

Abstract A unique one-pot reaction via CC cleavage from aminomethylene benzimidazoles with commercial halides to access novel benzimidazolones is reported for the first time. The previously unexploited transformation is able to perform smoothly in the presence of commercial potassium carbonate, while the stronger inorganic bases or organic amines as catalysts are not favorable to the transformation. Significant influential factors including base, temperature, solvent, water content, and molar ratio of substrates to this reaction are investigated, and possibly mechanistic consideration is also discussed. Some synthesized benzimidazolones were evaluated and exhibited better bioactivities against tested strains than clinical drugs chloromycin, norfloxacin, and fluconazole.

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