Annulation of Ethyl [Bis(ethylthio)methyl]benzoate and Ethyl 2-[1, 3]Dithiolan-2-yl-benzoate with α, β-Unsaturated Carbonyl Compounds : A New Synthesis of Naphthalene and Anthracene Derivatives

Yutaka OZAKI; Kazuhiro IMAIZUMI; Kyouko OKAMURA; Masahiro MOROZUMI; Ayako HOSOYA; Sang-Won KIM

doi:10.1248/cpb.44.1785

Yutaka OZAKI, Kazuhiro IMAIZUMI, Kyouko OKAMURA, Masahiro MOROZUMI, Ayako HOSOYA, Sang-Won KIM

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Keywords: [2C+4C] annulation, naphthalene, anthracene, tandem Michael-Claisen condensation, synthesis

JOURNAL FREE ACCESS

1996 Volume 44 Issue 10 Pages 1785-1789

DOI https://doi.org/10.1248/cpb.44.1785

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Abstract

Several kinds of fused cyclic compounds were obtained by tandem Michael-Claisen condensation of ethyl 2-[bis(ethylthio)methyl]benzoate and ethyl 2-[1, 3]dithiolan-2-yl-benzoate with α, β-unsaturated carbonyl compounds. Treatment of the annulated products with mercury(II)perchlorate trihydrate or N-chlorosuccinimide gave naphthoquinones, naphthalenes, and anthracenes.

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