A direct synthesis of 2,2-disubstituted 3-silylchromenes by [4+2] cycloaddition of in situ generated o-quinonemethides with electron-rich alkynes

Kenta Tanaka; Yujiro Hoshino; Kiyoshi Honda

doi:10.3987/COM-16-S(S)38

A direct synthesis of 2,2-disubstituted 3-silylchromenes by [4+2] cycloaddition of in situ generated o-quinonemethides with electron-rich alkynes

Kenta Tanaka, Yujiro Hoshino, Kiyoshi Honda

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

15 Citations (Scopus)

Abstract

A direct synthesis of 2,2-disubstituted 3-silylchromenes by [4+2] cycloaddition of in situ generated o-quinonemethides with electron-rich alkynes has been developed. The procedure is applicable for easily available starting materials like various substituted alkynylsilanes and salicylaldehydes. The present reaction provides versatile access to functionalized 2H-chromenes that would be a useful tool for the synthesis of biologically and photochemically active molecules.

Original language	English
Pages (from-to)	474-486
Number of pages	13
Journal	Heterocycles
Volume	95
Issue number	1
DOIs	https://doi.org/10.3987/COM-16-S(S)38
Publication status	Published - 2017
Externally published	Yes

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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author = "Kenta Tanaka and Yujiro Hoshino and Kiyoshi Honda",

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AU - Hoshino, Yujiro

AU - Honda, Kiyoshi

PY - 2017

Y1 - 2017

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AB - A direct synthesis of 2,2-disubstituted 3-silylchromenes by [4+2] cycloaddition of in situ generated o-quinonemethides with electron-rich alkynes has been developed. The procedure is applicable for easily available starting materials like various substituted alkynylsilanes and salicylaldehydes. The present reaction provides versatile access to functionalized 2H-chromenes that would be a useful tool for the synthesis of biologically and photochemically active molecules.

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ER -

A direct synthesis of 2,2-disubstituted 3-silylchromenes by [4+2] cycloaddition of in situ generated o-quinonemethides with electron-rich alkynes

Abstract

ASJC Scopus subject areas

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