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Paper | Regular issue | Vol 57, No. 5, 2002, pp.791-809
Published online, 1st January, 1970
DOI: 10.3987/COM-02-9433
4-[3-Dimethylamino-1-(2-dimethylaminovinyl]prop-2-enylidene]-2-phenyl-1,3-oxazol-5(4H)-one and 5-[3-Dimethylamino-1-(2-dimethylaminovinyl)prop-2-enylidene]-3-methyl-2-thioxo-1,3-thiazolidin-4-one in the Synthesis of 1,4-Dihydropyridine Derivatives

Ales Hvala, Lucija Jukic Sorsak, Gorazd Sorsak, Urska Bratusek, Jurij Svete,* Nina Lah, Ivan Leban, and Branko Stanovnik*

*Faculty of Chemistry and Chemical Technology, University of Ljubljana, Askerceva 5, P.O. Box 537, SLO-1000 Ljubljana, Slovenia

Abstract

4-{3-Dimethylamino-1-[2-(dimethylamino)vinyl]prop-2-enylidene]-2-phenyl-1,3-oxazol-5(4H)-one (3) and 5-{3-dimethylamino-1-[2-(dimethyl-amino)vinyl]prop-2-enylidene]-3-methyl-2-thioxo-1,3-thiazolidin-4-one (15) were prepared from 4-(1-methylethylidene)-2-phenyl-1,3-oxazol-5(4H)-one (2) and 5-(1-methylethylidene)-2-thioxo-1,3-thiazolidin-4-one (11), respectively. Treatment of compounds (3) and (15) with primary amines afforded 1,4-dihydropyridine derivatives (5) and (16) in 19-94% yields. Reactions of oxazolones (5) with hydrazine hydrate gave the corresponding imidazolones (6), while upon base- or acid-catalysed methanolysis of 5 methyl (benzoylamino)(1-substituted pyridin-4(1H)-ylidene)acetates (7) were obtained. Catalytic hydrogenation of 7a furnished α-(piperidin-4-yl)glycine derivative (8) and/or α-(pyridin-2-yl)glycine derivative (9).