Base-controlled selectivity in the synthesis of linear and angular fused quinazolinones by a palladium-catalyzed carbonylation/nucleophilic aromatic substitution sequence

Jianbin Chen, Kishore Natte, Anke Spannenberg, Helfried Neumann, Peter Langer, Matthias Beller, Xiao Feng Wu

Research output: Contribution to journalArticlepeer-review

104 Scopus citations

Abstract

A new approach for the facile synthesis of fused quinazolinone scaffolds through a palladium-catalyzed carbonylative coupling followed by an intramolecular nucleophilic aromatic substitution is described. The base serves as the key modulator: Whereas DBU gives rise to the linear isomers, Et 3N promotes the preferential formation of angular products. Interestingly, a light-induced 4+4 reaction of the product was also observed.

Original languageEnglish
Pages (from-to)7579-7583
Number of pages5
JournalAngewandte Chemie International Edition in English
Volume53
Issue number29
DOIs
StatePublished - 14 Jul 2014
Externally publishedYes

Keywords

  • carbonylation
  • domino reactions
  • nucleophilic aromatic substitution
  • palladium catalysts
  • quinazolinones

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