SUR QUELQUES DÉRIVÉS PHOSPHORES DE LA SPERMINE

Abstract

The reaction of spermine with aromatic aldehyde leads to an equilibrated system between the bis imine form 1' and the hexahydropyrimidine form 1. In contrary the formaldehyde adduct of spermine exist only on the hexahydropyrimidine form 9. 1–1' is readily hydrolyzed by HCl with regeneration of the aldehyde and spermine. The NaBH₄, reduction of 1–1' leads to the dibenzyl spermine 8 and the phosphonate adducts 2 or 6 are obtained from 1–1' and a hydrogen phosphonate. These last two reactions failed with 9. Inversely 9 and 1–1' reacts equably well with tetramethyl chloro dioxaphospholane with formation of cyclic phosphinamidates 10 and 5. In the second case a kinetic intermediate 3 can be observed by ³¹P NMR.

Key Words:

• Protective group for spermine
• amino phosphonate
• phosphinamidate
• bis imine-hexahydropyrimidine equilibrium