Convenient synthesis of a simple coumarin from salicylaldehyde and Wittig reagent. II: Synthesis of bromo- and methoxycarbonylcoumarins

T. Harayama, K. Nakatsuka, Hiromi Nishioka, K. Murakami, N. Hayashida, H. Ishii

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

Reaction of salicylaldehydes (1) with carbethoxymethylenetriphenylphosphorane in diethylaniline under reflux gave coumarins (3) in moderate to high yield except 3-methoxycarbonylsalicylaldehyde (1e). The substituent effects are discussed. A substituent at C6 on 1 usually facilitated the formation of the coumarin ring regardless of its electronic character.

Original languageEnglish
Pages (from-to)2170-2173
Number of pages4
JournalChemical and Pharmaceutical Bulletin
Volume42
Issue number10
Publication statusPublished - 1994

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Keywords

  • bromocoumarin
  • coumarin synthesis
  • methoxycarbonylcoumarin
  • salicylaldehyde
  • substituent effect
  • Wittig reaction

ASJC Scopus subject areas

  • Chemistry(all)
  • Organic Chemistry
  • Drug Discovery
  • Pharmacology

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