@article{CsuetoertoekiSzatmariHeydenreichetal.2012,
  author    = {Csuetoertoeki, Renata and Szatmari, Istvan and Heydenreich, Matthias and Koch, Andreas and Starke, Ines and Fueloep, Ferenc and Kleinpeter, Erich},
  title     = {Novel piperidine-fused benzoxazino- and quinazolinonaphthoxazines-synthesis and conformational study},
  series = {TETRAHEDRON},
  volume    = {68},
  journal   = {TETRAHEDRON},
  number    = {31},
  publisher = {PERGAMON-ELSEVIER SCIENCE LTD},
  address   = {OXFORD},
  issn      = {0040-4020},
  doi       = {10.1016/j.tet.2012.05.048},
  pages     = {6284 -- 6288},
  year      = {2012},
  abstract  = {The reactions of 1-(amino(2-hydroxyphenyl)methyl)-2-naphthol (3) and 1-(amino(2-aminophenyl) methyl)-2-naphthol (6) with glutardialdehyde resulted in the formation of piperidine-fused benzox-azinonaphthoxazine 4 and quinazolinonaphthoxazine 7, respectively, both in diastereopure form. The full conformational search protocols of 4 and 7 were successfully carried out by NMR spectroscopy and accompanying molecular modelling; the global minimum-energy conformers of all diastereomers were computed, and the assignments of the most stable stereoisomers, G(tct)(1) for 4 and G(tct)(1) for 7, were corroborated by spatial NOE information relating to the H-7a-H-10a-H-15b and H,H coupling patterns of the protons in the flexible part of the piperidine moiety. Additionally, mass spectrometric fragmentation was investigated in collision-induced dissociation experiments. The elemental compositions of the ions were determined by accurate mass measurements. (C) 2012 Elsevier Ltd. All rights reserved.},
  language  = {en}
}