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Paper | Regular issue | Vol 75, No. 6, 2008, pp.1355-1370
Published online, 15th February, 2008
DOI: 10.3987/COM-07-11303
Synthesis of 8-Hydroxyimidazo[1,2-a]pyridine-2-carboxylic Acid and Its Derivatives

Uros Groselj, Jure Bezensek, Anton Meden, Jurij Svete,* Branko Stanovnik,* Marko Oblak, Petra Stefanic Anderluh, and Uros Urleb

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

Abstract

Two new imidazo[1,2-a]pyridines, 8-hydroxyimidazo[1,2-a]pyridine-2-carboxylic acid (4) and ethyl 8-hydroxyimidazo[1,2-a]pyridine-2-carboxylate (6) were prepared via cyclization of 2-aminopyridin-3-ol (1) with bromopyruvic acid (2) and ethyl bromopyruvate (3), respectively. 8-Hydroxyimidazo[1,2-a]pyridine-2-carboxylic acid (4) was successfully coupled with various amino acid derivatives via its active ester intermediate into the corresponding amides 22-27. O-protected ethyl 8-hydroxyimidazo[1,2-a]pyridine-2-carboxylate 11 was transformed into its hydrazide 13, acyl azide 14, and amide 15 derivatives.