Preparation of Furo[3,2-c]coumarins from 3-Cinnamoyl-4-hydroxy-2H-chromen-2-ones and Acyl Chlorides: A Bu3P-Mediated C-Acylation/Cyclization Sequence

Chia Jui Lee, Cheng Che Tsai, Shao Hao Hong, Geng Hua Chang, Mei Chun Yang, Lennart Möhlmann, Wen-Wei Lin

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

A Bu3P-mediated cyclization reaction of 3-cinnamoyl-4-hydroxy-2H-chromen-2-ones though electrophilic addition of acyl chlorides towards the synthesis of highly functionalized furo[3,2-c]coumarins bearing a phosphorus ylide moiety is described. These unprecedented cyclization reaction proceeds under mild reaction conditions within short reaction times (1 min to 1 h), and can be further applied in the synthesis of alkenyl-substituted furo[3,2-c]coumarins by the treatment with carbonyl electrophiles under basic conditions.

Original languageEnglish
Pages (from-to)8502-8505
Number of pages4
JournalAngewandte Chemie - International Edition
Volume54
Issue number29
DOIs
Publication statusPublished - 2015 Jul 13

Keywords

  • acylation
  • cyclizations
  • heterocycles
  • ylides
  • zwitterion

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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