Palladium-catalysed reactions of 8-hydroxy- and 8-benzyloxy-5,7- diiodoquinoline under aminocarbonylation conditions

Attila Takács, Antal Szilágyi, Péter Ács, László Márk, Andreia F. Peixoto, Mariette M. Pereira, László Kollár

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

Various 5-carboxamido-7-iodo-8-benzyloxyquinolines were synthesised via selective aminocarbonylation of 5,7-diiodo-8-benzyloxyquinoline in the presence of 'in situ' generated palladium(0) catalysts. Under similar conditions (50 °C, 80 bar CO), 5,7-bis(N-tert-butyl-glyoxylamido)-8-hydroxyquinoline was obtained using tert-butylamine as N-nucleophile. The unprotected 5,7-diiodo-8-hydroxyquinoline underwent dehydroiodination resulting in 8-hydroxyquinoline as the major product.

Original languageEnglish
Pages (from-to)2402-2406
Number of pages5
JournalTetrahedron
Volume67
Issue number13
DOIs
Publication statusPublished - Apr 1 2011

Keywords

  • 8-Hydroxyquinoline
  • Aminocarbonylation
  • Carbon monoxide
  • Iodo-aromatics
  • Palladium

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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