Synthesis and characterisation of N-functionalized enetetramines, and their properties

Two general routes are described for the synthesis of the title compounds from the reaction of, either the dimethyl acetal of N,N'-dimethylformamide and an appropriate N, N'bis(secondary amine), or sodium hydride (or potassium tert-butoxide) and 4,5-dihydroimidazolium salts. N-Functionalized enetetramines (3, 8) having 2-methoxyethyl or allyl substituent on the N-atom have been made. The reaction of this enetetramines with S-8 and Se, gave the corresponding cyclic chalcogeno ureas derivatives (4, 5). Treatment of potassium tert-butoxide with 1,1'-ethylene-3,3'-diallyldiimidazolidinium dibromide (7) afforded, either the enetetramine ( 8), or, alternatively, the amino-Claisen isomer (9). All new compounds were identified by H-1, C-13 NMR, FT-IR and micro analysis.