Tetrahedron Letters

Bis-imine primary amine protection of the dialkyltriamine, norspermidine

AS Culf, JA Melanson, RJ Ouellette, GG Briand

Index: Culf, Adrian S.; Melanson, Jennifer A.; Ouellette, Rodney J.; Briand, Glen G. Tetrahedron Letters, 2012 , vol. 53, # 26 p. 3301 - 3304

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Citation Number: 3

Abstract

This Letter details the particular use of salicylaldehyde (2-hydroxybenzaldehyde) for the regiospecific protection of primary amines in a representative polyamine, norspermidine (N- (3-aminopropyl) propane-1, 3-diamine) under mild reaction conditions in high yield. The lack of intramolecular hexahydropyrimidine formation allowed for subsequent N2-acylation and N2-alkylation reactions, typical of polyamine synthetic strategies.