Synthesis of hydroxylamine analogues of polyamides

Article abstract of DOI:10.1016/0040-4020(96)00836-8

Novel analogues of spermine and spermidine with terminal H₂N-CH₂-group substituted by H₂N-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 analogues, ω-[[(1'-ethoxy-ethylidene)amino]oxy]-poly-(iminomethylene) nitriles were reduced to amines by NaBT₄/CoCl₂ 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-) analogues of spermidine were also synthesised.