A novel facile solid-phase strategy for the synthesis of N,N′,N″-substituted guanidines

Kilburn, John P.; Lau, Jesper and Jones, Raymond C.F. (2002). A novel facile solid-phase strategy for the synthesis of N,N′,N″-substituted guanidines. Tetrahedron, 58(9) pp. 1739–1743.

DOI: https://doi.org/10.1016/S0040-4020(02)00033-9

Abstract

A new facile solid-phase synthesis of N,N',N"-substituted guanidines from an immobilised amine component is described. The resin-bound amine was reacted with di-(2-pyridyl)thionocarbonate to generate the isothiocyanate which was treated with aryl/alkyl amines to yield the corresponding resin-bound thiourea. Desulfurisation of the thiourea was readily achieved by treatment with triphenylphosphine dichloride, and further reaction with aryl/alkyl amines followed by acidic cleavage with trifluoroacetic acid yielded N,N',N"-substituted guanidines of excellent purity and in good yield. (C) 2002 Elsevier Science Ltd. All rights reserved.

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