β-Oxoanilides in heterocyclic synthesis : Synthesis of Some New Pyrimidine containing Sulphonamido moiety Derivatives

Butanamide derivative (1) coupls smoothly with arenediazonium salts to afford the hydrazone (3). The latter product reacts with dimethylformamide – dimethylacetal (DMF-DMA) and or malononitrile to afford the substituted 1,4dihydropyridazines (5,6). Several new pyran (8), thiophene (9), pyrazole (14) and isothiocyanate derivatives (17,18) have been synthesized by the reactions of butanamide with 4-chloro-benzylidenemalonitrile, malononitrile and elemental sulfur, and hydrazine hydrate respectively. Refluxing of butanamide (1) with p-chlorobenzaldhyde afforded compound (10). Treating butanamide derivative (1) with (DMF-DMA) afforded compound (11) and when reacting with triethylorthoformate and hydroxylamine hydrochloride afforded compounds (13, 15). Treating of sulfonamide with thiophosgene afforded isothiocyanate product (16) which on refluxing with p-toulidine or methanol afforded compounds (17, 18) respectively.