Facile Synthesis of Pyrrolyl 4-Quinolinone Alkaloid Quinolactacide by 9-AJ-Catalyzed Tandem Acyl Transfer-Cyclization of o-Alkynoylaniline Derivatives

Koya Saito, Masahito Yoshida, Hidehiro Uekusa, Takayuki Doi

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

The synthesis of pyrrolyl 4-quinolinone alkaloid, quinolactacide, and its analogues was successfully achieved using 9-azajulolidine (9-AJ)-catalyzed tandem acyl transfer-regioselective cyclization of N,N-diacyl-o-alkynoylaniline derivatives. In addition, this organocatalytic reaction was successfully utilized for the synthesis of a variety of 3-acyl-4-quinolinones in moderate-to-good yields. Mechanistic studies, including a time course nuclear magnetic resonance (NMR) experiment, indicated that the 1,4-addition of 9-AJ to an ynone system can be considered to be the rate-determining step in this quinolinone synthesis.

Original languageEnglish
Pages (from-to)4370-4381
Number of pages12
JournalACS Omega
Volume2
Issue number8
DOIs
Publication statusPublished - 2017 Aug 31

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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