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

doi:10.1248/cpb.42.2170

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 journal › Article › peer-review

31 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 language	English
Pages (from-to)	2170-2173
Number of pages	4
Journal	Chemical and Pharmaceutical Bulletin
Volume	42
Issue number	10
DOIs	https://doi.org/10.1248/cpb.42.2170
Publication status	Published - 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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10.1248/cpb.42.2170

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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 (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.",

keywords = "Keywords salicylaldehyde, Wittig reaction, bromocoumarin, coumarin synthesis, methoxycarbonyl-coumarin, substituent effect",

author = "Takashi Harayama and Kazumitsu Nakatsuka and Hiromi Nishioka and Kyoko Murakami and Naomi Hayashida and Hisashi Ishii",

year = "1994",

doi = "10.1248/cpb.42.2170",

language = "English",

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pages = "2170--2173",

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T1 - Convenient Synthesis of a Simple Coumarin from Salicylaldehyde and Wittig Reagent. II

T2 - Synthesis of Bromo- and Methoxycarbonylcoumarins

AU - Harayama, Takashi

AU - Nakatsuka, Kazumitsu

AU - Nishioka, Hiromi

AU - Murakami, Kyoko

AU - Hayashida, Naomi

AU - Ishii, Hisashi

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 (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.

AB - 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.

KW - Keywords salicylaldehyde

KW - Wittig reaction

KW - bromocoumarin

KW - coumarin synthesis

KW - methoxycarbonyl-coumarin

KW - substituent effect

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JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

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

Abstract

Keywords

ASJC Scopus subject areas

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