Synthesis and Characterization of New Heterocyclic Compounds based on 5,5-dithio bis (1,3,4-thiadiazole -2- amine)

Abstract

     The parent compound (5,5-dithio bis(1,3,4-thiadiazole -2- amine)  was diazotized to afford the diazonium salt. Diazonium salts continue to attract great interest in the field of organic synthesis due to their various chemical and biological applications observed, especially in recent times. As a result, in this work new (16) compounds were synthesized in many steps. The first step was involved reaction of diazonium salt with active methylene compounds (malononitrile , ethyl cyanoacetate and ethyl acetoacetate) to give derivatives (1,2 and 3) ,respectively .Azide (4) was produced from treatment of diazonium with sodium azide , Moreover, cyclocondensation reaction of azide (4) with ethyl acetoacetate , malononitrile in presence of sodium ethoxide produce tetrazole derivatives (5,6), respectively ,(scheme 1) . Cyclization of compounds (1,2 and 3) were afforded a series of amino pyrazole and pyrazolone derivatives (7-12) ,(scheme 2). Furthermore, compound (6) was a good key for synthesis of new pyrrole, pyrazole and pyrimidine derivatives (13-16). The;;constructions;;of;all;manufactured ;combinations;;were confirmed; according;spectroscopic;;analysis such as UV, FTIR ,1HNMR and 13C-NMR .