Original approach to the construction of macrocyclic nitrogen heterocycles by means of complex palladium catalysts

The authors established for the first time that the reaction of ethylene imine with butadiene (1:2.5) in the presence of the Pd(acac)2-Ph3P-AlEt3-CF3CO2H (1:3:4:5) catalyst in methanol (1000C, 6 h) leads to the formation of N,N'-bis(2,7-octadienyl)piperazine (I), N,N',N''-tris(2,7-octadienyl)perhydro-1,4,7-triazacyclononane (II), and N,N',N'',N'''-tetrakis-(2,7-octadienyl)perhydro-1,4,7,10-tetraazacyclododecane (III) in a (I):(II-III) ratio of 13:87 and with an overall yield of 64%. In addition to compounds (I-III), the authors a 34% yield of N,N-bis(2,7-octadienyl)ethanolamine methyl ether. The mass spectra were obtained on a MX-1320 instrument at 70 and 12 eV. The PMR spectra were recorded on a Tesla BS-487B instrument in deuterochloroform with reference to TMS. The IR spectra were recorded on a UR-20 spectrophotometer for films