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Paper | Regular issue | Vol 60, No. 5, 2003, pp.1161-1172
Published online, 17th March, 2003
DOI: 10.3987/COM-03-9722
Transformations of Methyl 2-Benzoylamino-2-oxobutanoate. The Synthesis of Oxazolo[4,5-c]quinoline and 1-Substituted 1H-Imidazole-4-carboxylate Derivatives

Urska Bratusek, Simon Recnik, Jurij Svete,* Anton Meden, and Branko Stanovnik*

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

Abstract

Methyl 2-benzoylamino-2-oxobutanoate (1) was transformed with aromatic amines (2a-d) into methyl 2-arylamino-2-(benzoylamino)but-2-enoates (3a-d) Cyclization of compounds (3a-c) in polyphosphoric acid affords a mixture of oxazolo[4,5–c]quinoline derivatives (4a-c) and 1-aryl-2-phenyl-5-methyl-1H-imidazole-4-carboxylates (5a-c), while compound 3d gives a mixture of 9-bromo- (4d) and 7-bromooxazolo[4,5–c]quinoline derivative (4d’).