Intramolecular cyclization of alkynyl α-ketoanilide utilizing [1,2]-phospha-brook rearrangement catalyzed by phosphazene base

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Abstract

A novel catalytic cyclization reaction of alkynyl α-ketoanilide was developed by utilizing the [1,2]-phospha-Brook rearrangement. This reaction involves the generation of an amide enolate via the umpolung process, that is the addition of dialkyl phosphite to a keto moiety followed by the [1,2]-phospha-Brook rearrangement, and the subsequent intramolecular addition of the enolate to an alkyne to afford 3,4-dihydro-2-quinolone derivatives. Under high-temperature reaction conditions, further rearrangement of the allylic phosphate moiety occurs to provide 2-quinolone derivatives.

Original languageEnglish
Pages (from-to)3528-3531
Number of pages4
JournalOrganic letters
Volume16
Issue number13
DOIs
Publication statusPublished - 2014 Jul 3

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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