The thioxopyridine derivative (2) on treatment with ethyl chloroacetate gave the corresponding ethyl 3-aminothieno [2,3-b]pyridin-2carboxylate (3). Condensation of 3 with Ac 2 O gave the corresponding 4-H-pyrido[3',2':4,5]thieno[3,2-d] [1,3]oxazine derivative (4). Reaction of 4 with bifunctional groups gave 3,4dihydropyrido[3',2':4,5]thieno[3,2-d]pyrimidines (5 a,b) and 2-carbamoyl-3-acetamidothieno[2,3-b]pyridine derivative (6). Intramolecular cyclization of 6 by Ac 2 O/AcOH gave (7). Reaction of 5b with different electrophilic reagents were studied. Also, 5a upon treatment with ethyl chloroacetate and/or methyl iodide (K 2 CO 3) furnished the corresponding Nethylacetate (13) and N-methyl derivative (16) respectively. Hydrazinolysis of 13 gave the corresponding acetohydrazide (14) which on treatment with benzaldehyde furnished the corresponding 1H-pyrazol-4-yl derivative (15). The IR, 1 H NMR and MS spectra of newly derivatives were discussed. The antitumor activity against the liver tumor cell line HepG 2 of the prepared compounds were tested. Compounds 8a, 14 were more potent (IC 50 = 2.75 and 2.12 g/ml) than the standard drug (IC 50 = 4.60 g/ml).

Interaction of 4-aminoacetophenone (1) with p-tolyl sulphonamide afforded 1-[4-tosyl amino) phenyl]ethanone (2).Treatment of 2 with bromine water yielded 2-bromo-1-[4-tosyl amino) phenyl]ethanone (3), which reacted with thiourea to give 2-amino thiazole derivative (4). Compound 2 was condensed with phenyl acetaldehyde and malononitrile to give derivatives ( 5) and ( 7), which were respectively reacted with o-aminothiophenol and carbon disulfide to give derivatives ( 6) and ( 9). Reaction of 7 under Gewald reaction condition afforded the thiophen-3-carbonitrile derivative (11) which consequently reacted with 4fluorobenzylidinemalononitrile, phenyl isothiocyanate to give compounds 12 and 15, respectively. The structures of these compounds were confirmed by infrared, mass and 1 H-NMR spectra. The measurement of potential cytotoxicity for the compound 11 was tested and has exhibit anticancer of liver and breast.

Reactions of 3-methyl-1-phenyl-4,6-dihydroimidazo[4,5-c]pyrazole-5(1H)-thione with carbonyl compounds gave the arylidene derivatives 2 and 3, with recinoleic acid, phosphorus oxychloride/phosphorus pentachloride mixture and copper bronze gave the adduct 4, the chloro derivative 5 and the dimer with desulfurization 7. The behaviour of the chloroderivative towards hydrazine and primary amines have also been studied. On the other, reaction of 5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one with aromatic aldehydes gave the arylidene derivatives 8a-d, which on reaction with thiourea gave the pyrazolopyrimidinethione derivatives 9. The behaviour of compounds 9 towards copper bronze, sodium nitrite/acetic acid mixture, acrylonitrile and formaldehyde/ morpholine and its reaction with compound 1 in presence of copper bronze have also been taken into consideration.

Reaction of 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one with diazotized aromatic amines gave the corresponding diazenyl derivatives 1, which were condensed with carbonyl compounds to give the arylidene derivatives 2. Reaction of the parent pyrazolone with urea, thiourea and guanidine gave the pyrazoloimidazole derivatives 3. compound 3a reacted with thiourea in DMF to give the thiourea derivative 4. The reaction of 4 with malonic acid and acetyl chloride gave the pyrimidinedione derivative 5, which on reaction with thiourea in presence of sodium ethoxide gave the triazine derivative 6. S-alkylation of 6 with ethyl chloroacetate gave the ethyl acetate derivative 7, which on hydrolysis gave the corresponding acid, derivative8 and on reaction with hydrazine hydrate gave the corresponding acetohydrazide 9. the reaction of compound 9 with salicylaldehyde gave the pynazolidinone 10, while with carbon disulphide in alkaline solution it gave the oxadiazole thione 11 respectively. Some of the new compounds showed antimicrobial and antitumor activities.

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