2-Aminobenzimidazole and -benzoxazole as N-nucleophile in palladium-catalysed aminocarbonylation

Máté Gergely, Attila Bényei, László Kollár

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Abstract

Palladium-catalysed aminocarbonylation of aryl iodides in the presence of 2-aminobenzimidazole and 2-aminobenzoxazole as N-nucleophile was carried out. Single CO insertion took place, however, instead of the expected carboxamides (C(O)NH) the corresponding N-acyl-imine (C(O)N[dbnd]C) derivatives were obtained. The structure of the latter compounds can be explained by tautomerization involving the heterocyclic ring. The above structures without amide-NH moieties were proved by methylation at the NH groups of the heterocycle. The resulted mono- and dimethylated benzimidazole derivatives, as well as monomethylated benzoxazole derivatives, like the parent N-acylated compounds, were fully characterised including single crystal X-ray crystallography.

Original languageEnglish
Article number131079
JournalTetrahedron
Volume76
Issue number14
DOIs
Publication statusPublished - Apr 3 2020

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Keywords

  • Carbon monoxide
  • Carbonylation
  • Palladium
  • Tautomerization
  • Triazole

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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