Organophosphane-catalyzed direct β-acylation of 4-arylidene pyrazolones and 5-arylidene thiazolones with acyl chlorides

Pankaj V. Khairnar, Yin Hsiang Su, Yung Chang Chen, Athukuri Edukondalu, Yi Ru Chen, Wenwei Lin

Research output: Contribution to journalArticle

Abstract

An efficient method for the direct β-acylation of arylidene pyrazolones and thiazolones with acyl chlorides in the presence of a base catalyzed by organophosphanes is reported. A variety of functionalized 4-arylidene pyrazolone and 5-arylidene thiazolone derivatives were prepared under metal-free and mild conditions via a tandem phospha-Michael addition/O-acylation/intramolecular cyclization/rearrangement sequence. Our mechanistic investigations revealed that the reaction is highly stereospecific to provide exclusively cis-isomers, and the methodology can also be scaled up with similar efficacy.

Original languageEnglish
Pages (from-to)6868-6872
Number of pages5
JournalOrganic Letters
Volume22
Issue number17
DOIs
Publication statusPublished - 2020 Sep 4

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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