Convenient Synthesis of a Simple Coumarin from Salicylaldehyde and Wittig Reagent. II: Synthesis of Bromo- and Methoxycarbonylcoumarins

Takashi Harayama, Kazumitsu Nakatsuka, Hiromi Nishioka, Kyoko Murakami, Naomi Hayashida, Hisashi 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 (le) as summarized in Table I. 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
DOIs
Publication statusPublished - Jan 1 1994

Keywords

  • Keywords salicylaldehyde
  • Wittig reaction
  • bromocoumarin
  • coumarin synthesis
  • methoxycarbonyl-coumarin
  • substituent effect

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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