Synthesis of 4-ethyl-5-ethylimino-[1,2,4]-dithiazolidin-3-trithione through ethyl-(4-ethyl-5-thioxo-[1,2,4]-dithiazolidin-3-ylidene)ammonium oxopentachlorotungstate(VI) hydrolysis and the dimroth rearrangement in it on heating

Abstract

We demonstrate that the previously synthesized product of ethyl isothiocyanate insertion into tungsten hexachloride, WCl 5 {N(Et)C(S)N(Et)C(S)Cl}, whose partial hydrolysis yields {N(Et)C(S)-S-S-C=NH(Et)}[WOCl 5 ] (I), can be used as a source of biologically active heterocyclic compounds. 1 H and 13 C NMR and gas chromatography-mass spectrometry data show that reaction of I with a saturated aqueous Na 2 CO 3 solution yields a number of thiazolidine heterocycles, mostly 4 ethyl 5 ethylimino [1,2,4] dithia zolidin 3 trithione. The thermal Dimroth rearrangement leads to the formation of 2,4 diethyl [1,2,4] dithi azolidin 3,5 dithione and the products of partial hydrolysis of both heterocycles: 4 ethyl 5 ethylimino [1,2,4] dithiazolidin 3 on and 2,4 diethyl 3 thioxo [1,2,4] dithiazolidin 5 on.