Concise Synthesis of Heterocycle-Fused Naphthoquinones by Employing Sonogashira Coupling and Tandem Addition-Elimination/Intramolecular Cyclization

Kazunori Ueda; Mitsuaki Yamashita; Koichi Sakaguchi; Harukuni Tokuda; Akira Iida

doi:10.1248/cpb.c13-00102

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Concise Synthesis of Heterocycle-Fused Naphthoquinones by Employing Sonogashira Coupling and Tandem Addition-Elimination/Intramolecular Cyclization

Kazunori Ueda, Mitsuaki Yamashita, Koichi Sakaguchi, Harukuni Tokuda, Akira Iida

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Keywords: naphthoquinone, addition-elimination, intramolecular cyclization

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2013 Volume 61 Issue 6 Pages 648-654

DOI https://doi.org/10.1248/cpb.c13-00102

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Abstract

A concise method for the synthesis of heterocycle-fused naphthoquinones such as naphtho[2,3-b]-furan-4,9-dione, 1H-benz[f]indole-4,9-dione, and naphtho[2,3-b]thiophene-4,9-dione was developed. This method employed Sonogashira coupling and tandem addition-elimination/intramolecular cyclization, and it enabled the preparation of versatile heterocycle-fused naphthoquinones from one substrate.

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