Synthesis, Characterization And Reactions Of Trithiocarbonate And Aryl Acylguanidine Derivatives

Taking XC(=X)-X as the core structure, we carried out the synthesis and relevant reactions of trithiocarbonate (containing S-C(=S)-S) and aryl acylguanidine (containing N-C(=N)-N).Dibenzyl trithiocarbonate (DBTTC) and bis-(1-phenylethyl) carbonotrithioate (BPTTC) were prepared by one-pot method and characterized with FT-IR and1H NMR. Coordination reaction of DBTTC and bis(carboxymethyl) trithiocarbonate (BCMTTC) with transition metal salts were performed. One-dimensional coordination polymer [(PhCH2S)2CS-CuCl]n was obtained by stirring DBTTC and CuCl2in the mixed solution of ethyl acetate and ethanol. During the reaction CuCl2was reducted to CuCl. Other reactions didn’t give any characterizable product.Four different arylthioureas along with various primary and secondary amines were used as raw materials. NaBiO3and BiI3were employed as catalysts to synthesize aryl acylguanidine. Among these reactions, PhCON=C[N(H)Ar]N(H)CH2Ph (1, Ar=2,6-Me2C6H3;2, Ar=2,6-iPr2C6H3) were obtained by the treatment of arylthioureas and primary amine. The reactions involving secondary amines led to the formation of PhCON=C[N(H)Ar’]NCy2(3, Ar’=2,6-Me2C6H3), PhCO-N=C[N(H)Ar"]N(CH2Ph)2(4, Ar"=2,6-iPr2C6H3), Mes-CON=C[N(H)-Ar"]NCy2(5, Mes=2,4,6-Me3C6H2),1-Naph-CO-N=C[N(H)Ar"]NCy2(6), PhCON=C[N(H)Ar’]NEt2(7), PhCON=C[N(H)Ar"]NEt2(8), and PhCON=C[N(H)Ar"]N/Pr2(9). Aryl acylguaindines with equal arms of PhCON=C[N(H)Ar"]2(10) and PhCON=C[N(H)Ar’]2(11) were also synthesized. In the presence of diisopropylamine, acylthiourea PhCON(H)CSN(H)Ar’ may react with water to give acylurea PhCON(H)CON(H)Ar’(12).