Synthetic routes to N-Pmc-N′, N′′-disubstituted guanidines via EDCI-mediated guanylation of amines with N-Pmc-N′-substituted thioureas

S Flemer, JS Madalengoitia

Index: Flemer Jr., Stevenson; Madalengoitia, Jose S. Synthesis, 2007 , # 12 p. 1848 - 1860

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Citation Number: 8

Abstract

Abstract An overview of the facile and high-yielding EDCI-mediated reaction of amines with N-Pmc-N′-alkyl thioureas to afford guanidines is presented, in which the general scope and limitations of the reaction are probed. It was found that the N-sulfonyl-N′-substituted thioureas cannot possess internal nucleophiles or disubstitution, and that the incoming amine must possess adequate nucleophilicity in order for the reaction to be viable. ...