Optimised procedures for the one-pot selective syntheses of indoxyls and 4-quinolones by a carbonylative Sonogashira/cyclisation sequence

Marie Genelot, Anissa Bendjeriou, Véronique Dufaud, Laurent Djakovitch*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

41 Scopus citations

Abstract

A selective one-pot synthesis of carbonyl-containing N-heterocyclic compounds has been developed using a carbonylative Sonogashira/cyclisation sequence. Various catalytic protocols were studied (CO pressure, temperature, catalyst identity, base and substrate/catalyst ratio) with the objective of obtaining selectively either indoxyl or 4-quinolone products. The origin of the selectivity toward the 5- or 6-membered ring compounds was explained through the respective role of the various catalytic species involved, whether they are organic or metallic. The non-cyclic common intermediate was selectively prepared using [PdCl2(dppp)] as catalyst. By using a two-step multi-catalysis, i.e. {[Pd]+HNEt2}, 4-quinolones were obtained whereas with a tandem catalysis, i.e. {[Pd]/PR3}, indoxyls were synthesised.

Original languageEnglish (US)
Pages (from-to)125-132
Number of pages8
JournalApplied Catalysis A: General
Volume369
Issue number1-2
DOIs
StatePublished - Nov 15 2009
Externally publishedYes

Bibliographical note

Funding Information:
MG and AB are grateful to the National Agency of Research for financial support (No. ANR-07-BLAN-0167-01/02 ).

Keywords

  • 4-Quinolones
  • Carbonylative Sonogashira
  • Indoxyls
  • One-pot synthesis
  • Palladium catalysis

ASJC Scopus subject areas

  • Catalysis
  • Process Chemistry and Technology

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