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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 (Digital Object Identifier) Link: http://dx.doi.org/10.1016/S0040-4020(02)00033-9
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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.

Item Type: Journal Article
ISSN: 0040-4020
Keywords: N,N ',N ''-substituted guanidines; parallel synthesis; thioureas
Academic Unit/Department: Science > Life, Health and Chemical Sciences
Item ID: 6170
Depositing User: Astrid Peterkin
Date Deposited: 15 Feb 2007
Last Modified: 02 Dec 2010 19:55
URI: http://oro.open.ac.uk/id/eprint/6170
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