SYNTHESIS AND CHARACTERISATION OF N-FUNCTIONALIZED ENETETRAMINES, AND THEIR PROPERTIES
Engin Çetinkaya,b İsmail Özdemir,a
Bekir Çetinkaya,b and Michael F. Lappertc
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
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,Nbis(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