| Abstract: |
Synthesis and some reactions of 3[3`,5`-dinitrophenyl]-1,2,4-triazole-5-thiole derivatives .Treatment of compound (1) with ethyl chloroacetate in the presence of glacial acetic acid yielded the corresponding 3[3`,5`-dinitrophenyl]-5-carboxyethyl-methyl thio-1,2,4-triazoleCompound (1) was also subjected to the reaction with alkyl halide namely, methyl iodide , ethyl iodide and/or benzyl chloride in the presence of sodium hydroxide giving the corresponding S-alkyl derivatives (3 a-c) .Treatment of compound (2) with alcoholic solution of hydrazine hydrate and/or phenyl hydrazine afforded the corresponding acid hydrazides (4a-b) .The reaction of compound (4a) with aromatic aldehydes in acetic acid gave the hydrazone derivatives (5a-d) .Compound (5a-d) was cyclized by heating with acetic anhydride to yield the corresponding oxadiazolin derivatives (7 a-d) .Reaction of compound (4a) with phthalic anhydride in the presence of glacial acetic acid yielded the phthalazinone derivative (8) .Treatment of the acid hydrazide (4a) with ethyl chloroformate in boiling pyridine gave the corresponding 2[3(3`,5`-dinitrophenyl)-5-methylthio-1,2,4-triazol-5-yl]-1,3,4-oxadiazoline-5-one (9) .Also the acid hydrazide (4a) with carbon disulfide in the presence of KOH at 0oc in absolute ethanol to yield the potassium salt of dithiocarbazate (10).Cyclization of potassium salt of dithiocarbazate (10) by refluxing in absolute ethanol gave the corresponding 2-subistituted- 1,3,4-oxadiazoline 5-thione (11) .Treatment of the acid hydrazide (4a) with phenyl isothiocyanate inethanol yielded 1[3(3`,5`-dinitrophenyl)-1,2,4- triazole-5-thioacetate]-4-phenyl-3-thiosemicarbazide (12) .Cyclization of compound (12) depends on the nature of dehydrating agent 2-subistituted-5-phenylamino-1,3,4-thiadiazole (13) or 4-phenyl-3-subistituted-1,2,4-triazoline -5-thione (14) can be produced by using conc. sulphuric acid or 8% sodium hydroxide solThe reaction of triazole thiole (1) with secondary amine namely ,morpholine , N-methyl aniline , and / or piperidine in the presence of formaldehyde yielded N-mannish bases (15a-c).Treatment of 3,5dinitrophenylhydrazide ( 16 ) with carbon disulphide in presence of KOH at 0oC in absolute ethanol gave suspension of the potassium salt of dithiocarbazate derivative ( 17 ).Refluxing with stirring the potassium salt of dithiocarbazate ( 17 ) in ethanol yielded the corresponding 2(3`,5`-dinitrophenyl)-1,3,4-oxadiazol-5-thione (18).Treatment of 2(3`,5`-dinitrophenyl) 1,3,4-oxadiazol-5-thione ( 18 ) with primary aromatic amine namely aniline and/or p-toludine in boiling isopropanol afforded 3(3`,5`-dinitrophenyl)-4-phenyl or tolyl 1,2,4-triazoline-5-thiole ( 19 ).The reaction of 2(3`,5`-dinitrophenyl)-1,3,4-oxadiazol-5-thione ( 18 ) with anthranilic acid in boiling isopropanol gave the corresponding benzothiazine derivative ( 20 ).When ( 18 ) was allowed to react with hydrazine hydrate in ethanol the corresponding 3 (3`, 5`- dinitrophenyl)-4-amino-1,2,4-triazol-5-thiole was obtained ( 21 ).Refluxing ( 18 ) with hydroxylamine in boiling pyridine gave 3(3`,5`-dinitrophenyl)-4- hydroxyl-1,2,4-triazol-5-thiole ( 22 ).• The new heterocyclic compounds was analyzed and checked by IR and1H NMR spectra.• Part of this a thesis was published in The 8th International Conference on Chemistry and Its Role in Development Department of Chemistry Faculty of Science, Mansoura University Mansoura April 11-14,2005
|
|
|