Журнал "Макрогетероциклы"

Alexei A. Yakushev,^a,c Alexei D. Averin,^a,b@ Maxim V. Anokhin,^b Olga A. Maloshitskaya,^b Frédéric Lamaty,^c and Irina P. Beletskaya^a,b

^aA. N. Frumkin Institute of Physical Chemistry and Electrochemistry, 31 Leninskii prosp., Moscow, 119991, Russia.

^bLomonosov Moscow State University, Department of Chemistry, Leninskie Gory, 1-3, Moscow, 119991 Russia.

^cInstitut des Biomolécules Max Mousseron (IBMM) UMR 5247, Université Montpellier 2, Place Eugène Bataillon, 34095 Montpellier Cedex, France.

^@Corresponding author E-mail: alexaveron@yandex.ru

DOI: 10.6060/mhc141035a

Macroheterocycles 2014 7(4) 358-364

Cu(I)-catalyzed amination of N-(iodobenzyl) substituted azacrown ethers with propane-1,3-diamine and several polyoxadiamines was investigated. In the case of the diamine excess and the use of CuI/l-proline catalytic system in EtCN the formation of the compounds with one azacrown and one diamine moieties was observed. When taking the excess of N-(iodobenzyl) derivative of azacrown ether and CuI/2-(isobutyryl)cyclohexanone catalytic system in DMF, bis(azacrown) substituted oxadiamine could be obtained. Amination of N,N’-di(iodobenzyl) substituted diazacrown ether was studied under the same conditions. The comparison of Pd(0)- with Cu(I)-mediated amination reactions was done using N-(bromobenzyl) substituted azacrown ethers..

References: