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

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

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    30 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

    Keywords

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

    ASJC Scopus subject areas

    • Catalysis
    • Process Chemistry and Technology

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