SYNTHESIS AND CHARACTERISATION OF N-FUNCTIONALIZED ENETETRAMINES, AND THEIR PROPERTIES

Yetkin Gök,^a* Engin Çetinkaya,^b İsmail Özdemir,^a Bekir Çetinkaya,^b and Michael F. Lappert^c
a Inönü  University , Faculty Science and Art, Department of Chemistry, 44069  Malatya ,Türkiye
^b Ege University , Department of Chemistry, 35100 Bornova-İzmir, Türkiye
^c University of Sussex , Chem Lab., Brighton 9QJ, E Sussex ,  England

Abstract

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 S₈ 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 ¹H, ¹³C NMR, FT-IR and micro analysis.

Key words: enetetramines, imidazole, amino-Claisen rearrangement