New dioxadiaza-, trioxadiaza- and hexaaza-macrocycles containing dibenzofuran units

Li, F., Delgado, R., Coelho, A., Drew, M.G.B. and Felix, V. (2006) New dioxadiaza-, trioxadiaza- and hexaaza-macrocycles containing dibenzofuran units. Tetrahedron, 62 (36). pp. 8550-8558. ISSN 0040-4020 doi: 10.1016/j.tet.2006.06.073

Abstract/Summary

New dioxadiaza-, trioxadiaza-, and hexaaza-macrocycles containing rigid dibenzofuran groups (DBF) were prepared by a convenient synthetic route in high yields. The structures of the macrocycles were unequivocally established by electrospray mass spectrometry (ESIMS) studies together with NMR spectroscopy, with the exception of [14](DBF)N-3. The structures of the copper complex of [14](DBF)N-3 and of the diprotonated form of [22](DBF)N2O3 were determined by single crystal X-ray diffraction. Conformational analyses on the free macrocycles [14](DBF)N-3 and [22](DBF)N2O3 as well as on their larger counterparts containing two DBF units were undertaken in order to understand the synthetic findings. (c) 2006 Elsevier Ltd. All rights reserved.