Three-component synthesis of polysubstituted benzene derivatives via Diels-Alder reaction of cyclopentadienone acetal with alkyne

Sota Sato; Hiroyuki Isobe; Takatsugu Tanaka; Tomohiko Ushijima; Eiichi Nakamura

doi:10.1016/j.tet.2005.09.011

Three-component synthesis of polysubstituted benzene derivatives via Diels-Alder reaction of cyclopentadienone acetal with alkyne

Sota Sato, Hiroyuki Isobe, Takatsugu Tanaka, Tomohiko Ushijima, Eiichi Nakamura

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

28 Citations (Scopus)

Abstract

An efficient and regioselective synthesis of polysubstituted benzene derivatives was achieved via multicomponent reaction of a substituted cyclopropenone acetal and two alkyne molecules. The synthesis utilizes cyclopentadienone acetal as an intermediate and enables regioselective [2+2+2] assembly of the three-components into a benzene ring. A variety of polysubstituted benzene derivatives of synthetic and structural interest have been synthesized.

Original language	English
Pages (from-to)	11449-11455
Number of pages	7
Journal	Tetrahedron
Volume	61
Issue number	48
DOIs	https://doi.org/10.1016/j.tet.2005.09.011
Publication status	Published - 2005 Nov 28

Keywords

Cyclopentadiene
Cyclopropene
Diels-Alder reaction
Polysubstituted benzene
Three-component [2+2+2] synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2005.09.011

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title = "Three-component synthesis of polysubstituted benzene derivatives via Diels-Alder reaction of cyclopentadienone acetal with alkyne",

abstract = "An efficient and regioselective synthesis of polysubstituted benzene derivatives was achieved via multicomponent reaction of a substituted cyclopropenone acetal and two alkyne molecules. The synthesis utilizes cyclopentadienone acetal as an intermediate and enables regioselective [2+2+2] assembly of the three-components into a benzene ring. A variety of polysubstituted benzene derivatives of synthetic and structural interest have been synthesized.",

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AU - Sato, Sota

AU - Isobe, Hiroyuki

AU - Tanaka, Takatsugu

AU - Ushijima, Tomohiko

AU - Nakamura, Eiichi

PY - 2005/11/28

Y1 - 2005/11/28

N2 - An efficient and regioselective synthesis of polysubstituted benzene derivatives was achieved via multicomponent reaction of a substituted cyclopropenone acetal and two alkyne molecules. The synthesis utilizes cyclopentadienone acetal as an intermediate and enables regioselective [2+2+2] assembly of the three-components into a benzene ring. A variety of polysubstituted benzene derivatives of synthetic and structural interest have been synthesized.

AB - An efficient and regioselective synthesis of polysubstituted benzene derivatives was achieved via multicomponent reaction of a substituted cyclopropenone acetal and two alkyne molecules. The synthesis utilizes cyclopentadienone acetal as an intermediate and enables regioselective [2+2+2] assembly of the three-components into a benzene ring. A variety of polysubstituted benzene derivatives of synthetic and structural interest have been synthesized.

KW - Cyclopentadiene

KW - Cyclopropene

KW - Diels-Alder reaction

KW - Polysubstituted benzene

KW - Three-component [2+2+2] synthesis

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JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

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ER -

Three-component synthesis of polysubstituted benzene derivatives via Diels-Alder reaction of cyclopentadienone acetal with alkyne

Abstract

Keywords

ASJC Scopus subject areas

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