Diversity-oriented microwave-assisted synthesis of the 3-benzazepine framework

Vsevolod A. Peshkov, Olga P. Pereshivko, Pavel A. Donets, Vaibhav P. Mehta, Erik V. Van Der Eycken

Research output: Contribution to journalArticlepeer-review

40 Citations (Scopus)

Abstract

An efficient diversity-oriented procedure for the two-step synthesis of 3-benzazepines is described. The CdI-catalyzed three-component coupling of an aldehyde, an alkyne and an amine (A3-couplingj provides the required propargylamines and assures the generation of diversity. The Pd-catalyzed intramolecular acetylene hydroarylation reaction selectively creates the seven-membered 3-benzazepine framework with full control over the ring size and the geometry around the double bond. Microwave irradiation is demonstrated to be highly efficient in promoting both steps.

Original languageEnglish
Pages (from-to)4861-4867
Number of pages7
JournalEuropean Journal of Organic Chemistry
Issue number25
DOIs
Publication statusPublished - Sep 1 2010
Externally publishedYes

Keywords

  • C-C coupling
  • Cyclization
  • Medium-ring compounds
  • Microwave chemistry
  • Nitrogen heterocycles

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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