Synthesis of N-(thio)phosphorylated thiosemicarbazides RC(S)NHP(X)(OiPr)2 (X = S, R = NH2N(Me)–; X = O, R = NH2N(Me)–, PhNHNH–): Reaction of NH2N(Me)C(S)NHP(S)(OiPr)2 with acetone

Three new N-(thio)phosphorylated thiosemicarbazides of the common formula R–C(S)–NH–P(X)(OiPr)2 [X = S, R = NH2N(Me)– (1); X = O, R = NH2N(Me)– (2), PhNHNH– (3)] have been synthesized and characterized by NMR spectroscopy. The structures of the thiosemicarbazides 1–3 in CDCl3 and acetone-d6 solutions have been discussed in comparison with the N-(thio)phosphorylated thioureas Me–NH–C(S)–NH–P(X)(OiPr)2 [X = S (4), O (5)]. Reaction of 1 with acetone leads to the formation of the five-membered substituted 1,3,4-thiadiazolidine (6).

Three new N-(thio)phosphorylated thiosemicarbazides of the common formula R–C(S)–NH–P(X)(OiPr)2 [X = S, R = NH2N(Me)– (1); X = O, R = NH2N(Me)– (2), PhNHNH– (3)] have been synthesized and characterized by NMR spectroscopy. The structures of the thiosemicarbazides 1–3 in CDCl3 and acetone-d6 solutions have been discussed in comparison with the N-(thio)phosphorylated thioureas Me–NH–C(S)–NH–P(X)(OiPr)2 [X = S (4), O (5)]. Reaction of 1 with acetone leads to the five-membered substituted 1,3,4-thiadiazolidine (6).Figure optionsDownload as PowerPoint slideFigure optionsDownload as PowerPoint slide