Imidazo[1,2]hetarylglyoxylates: Synthesis and Reactivity toward Nucleophiles

A practical approach to imidazo[1,2]hetarylglyoxylates via Friedel-Crafts acylation of the parent fused imidazoles with ethyl oxalyl chloride is reported. The reaction is strongly influenced by the electron-donating properties of the starting heterocycle. The generated imidazo[1,2]hetarylglyoxylates undergo standard transformations typical of α-keto esters upon reaction with various nucleophiles. All the products contain an imidazoheterocyclic scaffold which is considered a privileged structure for drug discovery.

Zamkova I. A.; Chekotylo O. O.; Geraschenko O. V.; Grygorenko O. O.; Mykhailiuk P. K.; Tolmachev A. A.
Synthesis 2010, 10, 1692-1696
DOI: 10.1055/s-0029-1218739