Bis-imine primary amine protection of the dialkyltriamine, norspermidine

Bis-imine primary amine protection of the dialkyltriamine, norspermidine

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 hexahydrop...

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Veröffentlicht in:Tetrahedron letters 2012-06, Vol.53 (26), p.3301-3304
Hauptverfasser: Culf, Adrian S., Melanson, Jennifer A., Ouellette, Rodney J., Briand, Glen G.
Format: Artikel
Sprache:eng
Schlagworte:
Amines
Formations
Imine
Polyamine
Polyamines
Protection
Strategy
Tetrahedrons
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Beschreibung
Zusammenfassung: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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2012.04.070