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

29 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

Fingerprint

Coumarins
salicylaldehyde
coumarin

Keywords

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

ASJC Scopus subject areas

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

Cite this

Convenient synthesis of a simple coumarin from salicylaldehyde and Wittig reagent. II : Synthesis of bromo- and methoxycarbonylcoumarins. / Harayama, T.; Nakatsuka, K.; Nishioka, Hiromi; Murakami, K.; Hayashida, N.; Ishii, H.

In: Chemical and Pharmaceutical Bulletin, Vol. 42, No. 10, 1994, p. 2170-2173.

Research output: Contribution to journalArticle

@article{cfab8a9dd0054f388ae3fd33c3962d0e,
title = "Convenient synthesis of a simple coumarin from salicylaldehyde and Wittig reagent. II: Synthesis of bromo- and methoxycarbonylcoumarins",
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.",
keywords = "bromocoumarin, coumarin synthesis, methoxycarbonylcoumarin, salicylaldehyde, substituent effect, Wittig reaction",
author = "T. Harayama and K. Nakatsuka and Hiromi Nishioka and K. Murakami and N. Hayashida and H. Ishii",
year = "1994",
language = "English",
volume = "42",
pages = "2170--2173",
journal = "Chemical and Pharmaceutical Bulletin",
issn = "0009-2363",
publisher = "Pharmaceutical Society of Japan",
number = "10",

}

TY - JOUR

T1 - Convenient synthesis of a simple coumarin from salicylaldehyde and Wittig reagent. II

T2 - Synthesis of bromo- and methoxycarbonylcoumarins

AU - Harayama, T.

AU - Nakatsuka, K.

AU - Nishioka, Hiromi

AU - Murakami, K.

AU - Hayashida, N.

AU - Ishii, H.

PY - 1994

Y1 - 1994

N2 - 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.

AB - 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.

KW - bromocoumarin

KW - coumarin synthesis

KW - methoxycarbonylcoumarin

KW - salicylaldehyde

KW - substituent effect

KW - Wittig reaction

UR - http://www.scopus.com/inward/record.url?scp=0027941895&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0027941895&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:0027941895

VL - 42

SP - 2170

EP - 2173

JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

SN - 0009-2363

IS - 10

ER -