Synthesis and characterization of some tetracyclic spermine derivatives of cyclotriphosphazene: the first examples of dispiransa derivatives

Abstract

The synthesis and characterization is reported of a series of dispiransa cyclophosphazene derivatives based on the known compound N<inf>3</inf>P<inf>3</inf>X<inf>2</inf>[HN(CH<inf>2</inf>)<inf>3</inf>N(CH<inf>2</inf>)<inf>4</inf>N(CH<inf>2</inf>)<inf>3</inf>NH], (2) (where X = Cl), to give a number of new compounds (3a-g) in which X = Ph, PhS, PhNH, PhO, MeO, EtO, CF<inf>3</inf>CH<inf>2</inf>0, respectively. Two synthetic routes were utilized: (i) reaction of spermine with the appropriate disubstituted cyclophosphazenes (1) to give compounds (3a-c) and (ii) using the chloro-precursor (2) in nucleophilic substitution reactions with nucleophiles to give compounds (3d-g). The structures of the compounds were determined by elemental analysis, mass spectrometry, 1H and 31P NMR spectrocsopy. © 2008 The Japan Institute of Heterocyclic Chemistry. © 2009 Elsevier B.V., All rights reserved.