A new approach to the synthesis of 4-( N-aryl)carbamoylmethyl-4,5-dihydropyridazin-3(2 H)-ones

Reaction of N-aryl substituted maleimides with aliphatic ketazines leads to the formation of 4,5-dihydropyridazin-3(2 H)-ones in moderate yields. The reaction proceeds through 1,4-addition of an azine to the maleimide double bond, as confirmed by separation of the corresponding adducts in some cases, which are then converted into 4,5-dihydropyridazin-3(2 H)-ones. In addition, the solid-state synthesis of 4,5-dihydropyridazin-3(2 H)-ones is demonstrated for the first time.