Synthesis and molecular structure of bis(benzo)aza-14-crown-4 ethers with 7-azabicyclo[3.3.1]nonane and homologous fragments

By condensation of cycloalkanes with 2-{2-[2-(2-formylphenoxy)ethoxy] ethoxy}benzaldehyde and ammonium acetate by Petrenko-Kritchenko method first representatives of new heterocyclic systems, bis(benzo)-aza-14-crown-4 ethers containing a 7-aza-bicyclo[3.3.1]nonane or its homologous fragment, were obtained in 6-15% yield. With growing cycle of the initial cycloketone the yield of the azacrownophane considerably grew. By means of XRD analysis the molecular structure was established of four synthesized macrocycles, the relative configuration of asymmetrical atoms was determined, and the size of the internal cavities of the azacrown part was estimated. © 2008 MAIK Nauka