Synthesis of Hydroxylamine Analogues of Polyamines

Abstract Novel analogues of spermine and spermidine with terminal H 2 NCH 2 -group substituted by H 2 NO-group, were prepared starting the synthesis from EtO(Me)CNOH and subsequent extension of a polyamine backbone. To prepare their earlier unknown tritium labelled analoques, ω-[[(1′-ethoxyethylidene)amino]oxy]-poly-(iminomethylene) nitriles were reduced to amines by NaBT 4 CoCl 2 complex, which did not effect the N-O or CN bonds of ethoxyethylidene group, whereas aminooxy group deprotection was performed at the final step of synthesis by mild acidic hydrolysis. Novel monoacetylated (AcHN- or AcNHO-) analoques of spermidine were also synthesised.