Through cyclization of 4-(dichloromethylene)-5-(aminosulfonylimino)imidazolidin-2-ones by formaldehyde action series of 8-(dichloromethylene)-3,4,7,8-tetrahydro-6H-imidazo[5,1 c][1,2,4,6]-thiatriazin-6-one 2,2-dioxides were synthesized. The PMB-deprotection from the 3rd position of created heterocyclic system and further 3N-alkylation were realized. Their structure parameters were discovered by NMR experiments and X-Ray analysis. The separate products (with allyl, carbethoxymethyl, 2-N-Boc-aminoethyl, 2-(N-Boc-N-isopropoxymethylamino)ethyl substituents in position 3) demonstrated high antiproliferative activity.

In this work, the indirect reductive amination of terephthalaldehyde with aqueous ammonia was studied. The condensation of terephthalaldehyde with ammonia afforded a new compound containing two aldehyde groups (CHO), one imino group (C=N), and an aminal carbon (N–CH–N). Reaction of this compound with sodium borohydride resulted in the reduction of the aldehyde groups, the imino carbon, and the aminal carbon. Analysis of the condensed Fukui functions and the LUMO orbital allowed us to propose a mechanism that explains this reactivity. Furthermore, a general mechanism for the condensation of aromatic aldehydes with aqueous ammonia is presented.