Homogeneous catalytic aminocarbonylation of nitrogen-containing iodo-heteroaromatics. Synthesis of N-substituted nicotinamide related compounds

Attila Takács, Balázs Jakab, Andrea Petz, László Kollár

Research output: Contribution to journalArticle

35 Citations (Scopus)

Abstract

Various primary and secondary amines, including amino acid methyl esters, were used as nucleophiles in palladium-catalysed aminocarbonylation of 2-iodopyridine, 3-iodopyridine and iodopyrazine. N-Substituted nicotinamides and 3-pyridyl-glyoxylamides (2-oxo-carboxamide type derivatives) of potential biological importance can be obtained from 3-iodopyridine as a result of simple and double carbon monoxide insertions, respectively. The latter examples can be obtained in synthetically acceptable yields by using elevated carbon monoxide pressure. On the contrary, N-alkyl/aryl-carboxamides were obtained exclusively in the whole pressure range by using 2-iodopyridine and iodopyrazine.

Original languageEnglish
Pages (from-to)10372-10378
Number of pages7
JournalTetrahedron
Volume63
Issue number41
DOIs
Publication statusPublished - Oct 8 2007

Keywords

  • Amino acid
  • Aminocarbonylation
  • Carbon monoxide
  • Palladium
  • Pyridine

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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