Abstract
A series of heterocylic compounds was synthesized from 1-(3,4-dimethoxyphenyl)-3-(4-ethoxyphenyl) prop-2-en-1-one 1, which was reacted with thiourea, ethyl acetoacetate, p-nitro-phenylhydrazine and hydroxylamine hydrochloride afforded thioxopyrimidine 2, tetrahydro-terphenyl 3, 1,3,5-triarylpyrazole 4, and 3,5-diarylisoxazole 5 derivatives, respectively. While, upon reaction of thioxopyrimidine 2 with piperidine, anthranilic acid or hydrazine hydrate afforded piperidin-1-yl-1,4-dihydropyrimidine 6, pyrimido[2,1-b] quinazoline 7 and 2-hydrazinyl-1,4-dihydropyrimidine 8 derivatives, respectively. Finally, the latter compound 8 was heterocyclized with formic acid, acetic anhydride, carbon disulfide, acetyl acetone or phthalic anhydride resulting the corresponding triazolo[4,3-a] pyrimidines 9, 10, 11, pyrazolyl pyrimidine 12 and imide derivatives 13, respectively. The structural assignments of new compounds were based on their elemental analysis and spectral (IR, H-1 NMR and C-13 NMR) data. All the newly substituted pyrimidine, isoxazole, pyrazole and fused tria-zolopyrimidine derivatives displaying potential analgesic and anti-convulsant activities.