Abstract The reaction pathway of 4-aroyl-3-hydroxy-2 (5H)-furanones 1 with diamines depends on the nature of the amine as well as on the applied reaction conditions. Thus, the reaction of 1a-d with 5, 6-diamino-1, 3-dimethyluracil 5 led to the formation of two isomeric Schiff bases 7a-d and 8a-d. Conversely type 1 compounds reacted with 4, 5- diaminopyrimidine 9 or 2, 3-diaminopyridine 10 to form the mono acid-base adducts 11a ...