High-yielding synthesis of 1-isoindolinone derivatives via palladium-catalysed cycloaminocarbonylation

Diána Marosvölgyi-Haskó, Attila Takács, Zsuzsanna Riedl, László Kollár

Research output: Contribution to journalArticle

43 Citations (Scopus)

Abstract

1-Isoindolinone derivatives were synthesised in high yields (up to 89%) by using 2-iodobenzyl bromide and 2-iodobenzylamine as bifunctional substrates in palladium-catalysed carbonylation. Depending on the N-nucleophiles, two types of compounds were synthesised with 2-iodobenzyl bromide: the use of primary amines, including amino acid methylesters, resulted in the formation of N-substituted 1-isoindolinones, while secondary amines react both with the benzyl bromide and iodoarene moieties resulting in the corresponding ortho-(N-piperidino/morpholinomethyl)-benzamides. The parent 1-isoindolinone was obtained in a facile, highly chemoselective intramolecular aminocarbonylation of 2-iodobenzylamine. The mechanistic details of the ring-closure reaction and the conditions leading to side-products are discussed as well.

Original languageEnglish
Pages (from-to)1036-1040
Number of pages5
JournalTetrahedron
Volume67
Issue number5
DOIs
Publication statusPublished - Feb 4 2011

Keywords

  • Amino acid
  • Aminocarbonylation
  • Carbon monoxide
  • Cyclocarbonylation
  • Lactam
  • Palladium

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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