Synthesis of tetralylthiazole dithiocarbamate and hydrazine derivatives

ABSTRACT

The interesting pharmacological properties of both tetraline and thiazole moities, led us to synthesize a new series of compounds incorporating both moities for the sake of getting compounds of possible biological activity. Thus, chloroacetylation of 2-amino-4-[2-tetralyl] thiazole [II] with chloroacetyl chloride in dry benzene afforded 2-chloroacetylamino4-[2-tetralyl] thiazole [III]. It serves as a useful starting material for the synthesis of dithiocarbamate derivatives known to be biologically active compounds. Compound II was prepared by the condensation of 2-bromoacetyItetralin [I] with thiourea. Furthermore, treatment of III with ammonium salt of substituted dithiocarbamic acids IV gave the corresponding dithiocarbamate derivatives, namely, S-[2-acylamino-4-[2-tetralyl]] thiazole-N-substituted dithiocarbamates Va-e. On the other hand, it has been reported that Schiff s bases are biologically active compounds. So, it is of interest to synthesize the Schiff's bases of 2-amino4-[2-tetralyl] thiazole [II]. Therefore, condensation of II with different aromatic aldehydes, yielded the corresponding arylidene derivatives Vla-c. In addition, 2-hydrazino-4-[2-teralyl] thiazole [VII] was obtained through the condensation of 6-bromoacetyltetralin [I] with 1-acetylthiosemicarbazide in ethanol followed by hydrolysis with hydrochloric acid The hydrazones Vllla-e were prepared either by the condensation of VII with different aromatic aldehydes or by the reaction of thiosemicarbazone derivatives IXa-e with compound I. Hydrazones VIHa-e were separated as their hydrobromides and all attempts to obtain the free hydrazone derivatives were unsuccessful and gave tarry products