A Novel Methodology for Synthesis of 1,5,6-Trisubstituted 2(1H)-Pyrazinones of Biological Interest

Ryosuke Saijo; Hiroshi Sekiya; Eiji Tamai; Ken-ichi Kurihara; Jun Maki; Hiroshi Sakagami; Masami Kawase

doi:10.1248/cpb.c16-00830

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A Novel Methodology for Synthesis of 1,5,6-Trisubstituted 2(1H)-Pyrazinones of Biological Interest

Ryosuke Saijo, Hiroshi Sekiya, Eiji Tamai, Ken-ichi Kurihara, Jun Maki, Hiroshi Sakagami, Masami Kawase

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Keywords: ring transformation, mesoionic, pyrazinone, isocyanide

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Supplementary material

2017 Volume 65 Issue 4 Pages 365-372

DOI https://doi.org/10.1248/cpb.c16-00830

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Abstract

In this report, we describe a new method for the synthesis of densely functionalized 2(1H)-pyrazinones. Treatment of mesoionic 1,3-oxazolium-5-olates with carbanions derived from activated methylene isocyanides (p-toluenesulfonylmethyl isocyanide (TosMIC) and ethyl isocyanoacetate) causes a novel ring transformation affording 2(1H)-pyrazinones in moderate to high yields. The cytotoxicity and antibacterial activity of some of the obtained products were studied and some of the products exhibited tumor-specific cytotoxicity.

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