A combinatorial synthetic route yielding imidazo[1,5-a]quinoxalines and pyrazolo[1,5-a] quinoxalines is described. The use of 2-fluoroaniline and 1H-imidazole-4-carboxylic acid, respectively, 1H-pyrazole-3-carboxylic acid in the Ugi-reaction (U-4CR) followed by a nucleophilic aromatic substitution (S(N)Ar) affords the imidazo- as well as the pyrazolo-[1,5-a] quinoxaline moiety in good yield and high diversity. (C) 2007 Elsevier Ltd. All rights reserved.