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

F. F. Mahmoud

Abstract

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 1,4- dihydropyridazines (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.