Synthesis of some new 1,3,4-oxadiazole derivatives from 4-{bis[3-(5-mercapto-1,3,4-oxadiazol-2-yl)‎-4-methoxy phenyl] methylene}-2-(5-mercapto-1,3,4-oxadiazol-2-yl)‎ cyclohexa-2,5-dienone

Abstract EN

In this research new tri (1, 3, 4-oxadiazole) derivatives [5-10] were prepared starting from 4-{bis [3- (5-mercapto-1, 3, 4-oxadiazol-2-yl) -4- methoxyphenyl] methylene}-2- (5-mercapto-1, 3, 4-oxadiazol-2-yl) cyclohexa-2, 5- dienone [4]. The triester derivative [2] obtained from treatment of 5, 5'- [(3-carboxy- 4-oxocyclohexa-2,5-dienylidene) methylene] bis (2-hydroxybenzoic acid) [1] with dimethyl sulphate in presence of anhydrous sodium carbonate in dry acetone which was then converted into the trihydrazide derivative [3] by reaction with hydrazine monohydrate in absolute ethanol.

Treatment of trihydrazide derivative [3] with carbon disulfide in presence of potassium hydroxide in absolute ethanol resulted in the formation of tri (1, 3, 4-oxadiazole) derivative [4] which was then converted into the trithioalkyl derivatives [5], [6] and [7] by reaction with benzyl chloride, n-butyl bromide and n-propyl bromide in basic medium, respectively.

Treatment of trithioalkyl derivatives [5], [6] and [7] with potassium permanganate in acidic medium resulted in the formation of trisulfone derivatives [8], [9] and [10], respectively.

These new synthesized compounds [2-10] probably have some biological activity. All new compounds were characterized by melting points and were uncorrected, (C.H.N.) Elementary Analysis and FT-IR spectra.