The reaction of malononitrile with chalcone: A controversial chemical process

Article abstract of DOI:10.1016/S0040-4039(00)92390-6

Given the significant discrepancies in the several reported results on the reaction of chalcone (1,3-diphenyl-2-propne-1-one) (1) with malononitrile (2), a careful reinvestigation was carried out. Depending upon the reaction conditions either the open-chain Michael adduct (4), an alkoxypyridine (5), an aminoisophthalonitrile (6) or a cyclohexanol (7) is obtained. However, no 4H-pyran could be isolated from this reaction.