Abstract

SYNTHESIS OF SOME NEW HETEROCYCLIC COMPOUNDS DERIVED FROM 2-NAPHTHOIC ACID AND 4-METHYL BENZOIC ACID

Tamara T. Fatah* and Amal N. Ali

ABSTRACT

In this paper, the acid hydrazides (2-naphthohydrazide,4-methyl benzohydrazide) is converted into substituted 1, 3, 4-oxadiazole-2(3H)-one (1, 2) when treated with ethyl chloroformate in n-butanol and then these compounds are converted to substituted 4-amino-2H-1, 2, 4-triazole-3(4H)-one (3, 4) when treated with hydrazine hydrate in n-butanol, and then hydrazides are converted to substituted potassium hydrazine-1-carbothioate (5, 6) by reaction with carbone disulfide and potassium hydroxide which is converted to substituted 1, 3, 4-thiadiazole-2 (3H)-thione (7, 8) and substituted 1, 3, 4-oxadiazole-2(3H)-thione (9,10) by treated with concentrated sulfuric acid and hydrochloric acid in absolute ethanol respectively. The two compounds 2-amino-5-substituted-1, 3, 4-thiadiazole (11, 12) which are prepared by treated substituted thiosemicarbazides with concentrated sulfuric acid converted to some substituted schiff bases (13-18) by reaction with benzaldehyde derivatives in ethanol and added drops of glacial acetic acid, the schiff bases derivatives product then converted to 2-(substituted)-3 (5-(4-methyl benzyl or naphthalene-2-yl)-1, 3, 4-thiadiazol-2-yl) thiazoliden-4-one (19-24) when treated with thioglycolic acid in presence of anhydrous zinc chloride in methanol. The structures of the synthesized compounds have been confirmed by physical and spectral data.

Keywords: 1, 3, 4-thiadiazole, 1, 2, 4-triazole, Schiff bases, thiazoliden.