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Chem Pharm Bull (Tokyo). 2017;65(4):365-372. doi: 10.1248/cpb.c16-00830.

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

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1
Faculty of Pharmaceutical Sciences, Matsuyama University.

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.

PMID:
28381677
DOI:
10.1248/cpb.c16-00830
[Indexed for MEDLINE]
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