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

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 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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Convenient Synthesis of a Simple Coumarin from Salicylaldehyde and Wittig Reagent. II : Synthesis of Bromo- and Methoxycarbonylcoumarins. / Harayama, Takashi; Nakatsuka, Kazumitsu; Nishioka, Hiromi; Murakami, Kyoko; Hayashida, Naomi; Ishii, Hisashi.

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

Research output: Contribution to journal › Article › peer-review

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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.",

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

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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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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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