Facile Synthetic Route to Selectively Protected Spermidine Homologues

Abstract

Several selectively protected spermidine homologues were synthesized via cyanoethylation reaction of monoprotected diamines, subsequent protection of their secondary amino group, hydrolysis of nitrile to primary amide function, and final Hofmann degradation of amides to amines with the aid of iodosobenzene diacetate (PIDA). The protected spermidine homologues may be directly used in the synthesis of polyamine amides or may be further functionalized.

Keywords:

• Hofmann degradation
• Michael addition
• polyamines
• protecting groups

Acknowledgment

The authors are indebted to the Faculty of Chemistry, Gdańsk University of Technology, Poland, for financial support.