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

Access to Document

10.1248/cpb.42.2170

Fingerprint Dive into the research topics of 'Convenient Synthesis of a Simple Coumarin from Salicylaldehyde and Wittig Reagent. II: Synthesis of Bromo- and Methoxycarbonylcoumarins'. Together they form a unique fingerprint.

Cite this

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

@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 (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",

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, 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

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

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

U2 - 10.1248/cpb.42.2170

DO - 10.1248/cpb.42.2170

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 -