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Paper | Special issue | Vol 49, No. 1, 1998, pp.133-142
Published online, 1st January, 1970
DOI: 10.3987/COM-97-S5
The Synthesis of Ethyl 2-(2-Cyano-2-ethoxycarbonylethenyl)amino-3-dimethylaminopropenoate. The Synthesis of Substituted Aminoazolo-, Aminoazinopyrimidinones and 2H-1-Benzopyran-2-ones

Lovro Selic, Simona Golic Grdadolnik, and Branko Stanovnik*

*Faculty of Chemistry and Chemical Technology, University of Ljubljana, Askerceva 5, 1000 Ljubljana, Slovenia

Abstract

Ethyl 2-(2-cyano-2-ethoxycarbonylethenyl)amino-3-dimethylaminopropenoate (3) was prepared in two steps from ethyl 2-cyano-3-ethoxypropenoate, and used as a reagent for the preparation of N-protected 3-amino-4H-pyrido[1,2-a]pyrimidin-4-ones (9a-c), 5H-thiazolo[3,2-a]pyrimidin-5-one (10), 4H-pyrido[1,2-a]pyridin-4-one (11), 2H-1-benzopyranones (12a,b), and their tetrahydro derivatives (13a,b). Free amino 4H-pyrido[1,2-a]pyrimidin-4-ones (14a-c), 5H-thiazolo[3,2-a]pyrimidin-5-one (15) and 4H-pyrido[1,2-a]pyridin-4-one (16), were prepared from 9-13 by removal of the 2-cyano-2-ethoxycarbonylethyl as N-protecting group by heating with hydrazine hydrate.