Facile synthesis of 1,8-naphthalimides in palladium-catalysed aminocarbonylation of 1,8-diiodo-naphthalene

Attila Takács, Péter Ács, László Kollár

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

1,8-Diiodo-naphthalene was aminocarbonylated with various primary and secondary amines in the presence of palladium(0) complexes formed in situ from palladium(II) acetate and triphenylphosphine. In the case of primary amines, depending on the amine to substrate ratio, two types of products have been obtained in highly chemoselective reaction: dicarboxamides and N-substituted imides have been formed at high and low amine to substrate ratio, respectively. The reaction tolerates the ester functionality, so that amino acid esters could serve as N-nucleophiles and in this way, naphthalimides possessing stereogenic centre in the N-substituent could be synthesised.

Original languageEnglish
Pages (from-to)983-987
Number of pages5
JournalTetrahedron
Volume64
Issue number6
DOIs
Publication statusPublished - Feb 4 2008

    Fingerprint

Keywords

  • Amine
  • Aminocarbonylation
  • Carbon monoxide
  • Carbonylation
  • Iodoaromatics
  • Palladium

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this