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