Synthesis, reactions and biological activity of some new thieno[2,3-f]-1,3-benzodioxoles.

The reaction of 7-chlorothieno[2,3-f]-1,3-benzodioxole-6-carbonyl chloride (2) with some aromatic or heterocyclic amines gave the corresponding 6-(aryl or heterocyclyl) carbamoyl-7-chlorothieno [2,3-f]-1,3-benzodioxoles (3a-c, 4a, b and 5). Compound 2 was also reacted with potassium thiocyanate, ethanol or sodium azide to afford the isothiocyanto compound 6, the ester 7 and the acid azide 9, respectively. Hydrazinolysis of 7 gave the carbohydrazide 8. The compounds 6, 8 and 9 were used as precursors in the synthesis of the target heterocycles, 7-chlorothieno[2,3-f]-1,3-benzodioxoles substituted with a variety of moieties at position-6 (10-15, 17, 19-26, 28-31). Also, 2-methyl-1,3-dixolo[5,6][1]benzothieno[2,3-c]quinolin- 6(5 H)-one (33) was prepared. The antibacterial and antifungal activities of some selected compounds were also reported.

Synthesis and anti-microbial activity of some imidazo[1',2':5,6]pyrimido[4,5-c]pyridazines and related heterocycles.

The synthesis of the title heterocycles was achieved using 3-amino-5,6-diphenylpyridazine-4-carbonitrile (4) as a starting material. This compound was converted into the corresponding 4-imidazolinyl derivative 5 which was then subjected to cyclization reactions to afford the title compounds.

Synthesis and antimicrobial activity of pyrazolo[3',4':4,3]pyrido[6,5-c]pyridazine and thieno[2,3-c]pyridazine derivatives.

4-Acetyl-5,6-diphenyl-2(H)pyridazine-3-one (1) was allowed to react with phenyl hydrazine to afford the corresponding hydrazone 2. Hydrazone 2 upon treatment with Vilsmeier's reagent gave pyrazolylpyridazine derivative 3, which was allowed to react with thiosemicarbazide and hydroxyl amine to give the corresponding thiosemicarbazone and oxime 4 and 5, respectively. Treatment of oxime 5 with Ac2O gave the pyrazolylpyridazine carbonitrile derivative 6. Compound 5 reacts with POCl3 to give the corresponding chloro compound 7. The chloro compound 7 was reacted with hydrazine hydrate or aniline to afford pyrazolopyridazodiazepine 9 or pyrazolopyridazopyridazine 10. When compound 1 was allowed to react with POCl3 the chloro derivative 11 resulted. This compound reacts with thiourea, piperidine or hydrazine hydrate to give compounds 12, 14 and 15, respectively. Compound 12 reacted with alpha-haloester or alpha-haloketone to give the thienopyridazines 13a and b, respectively. Most of the newly synthesized compounds were screened for fungicidal and bactericidal activity.