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-d(6) 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 I with acetone leads to the formation of the five-membered substituted 1,3,4-thiadiazolidine S-C(Me)(2)-NH-N(Me)-C=N-P(S)(OiPr)(2) (6). (C) 2009 Elsevier Ltd. All rights reserved.