TY  - JOUR
A1  - Csuetoertoeki, Renata
A1  - Szatmari, Istvan
A1  - Heydenreich, Matthias
A1  - Koch, Andreas
A1  - Starke, Ines
A1  - Fueloep, Ferenc
A1  - Kleinpeter, Erich
T1  - Novel piperidine-fused benzoxazino- and
 quinazolinonaphthoxazines-synthesis and conformational study
JF  - TETRAHEDRON
N2  - 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.
KW  - Quinazolines
KW  - Naphthoxazines
KW  - DFT structural study
KW  - Conformational analysis
KW  - NMR spectroscopy
Y1  - 2012
U6  - https://doi.org/10.1016/j.tet.2012.05.048
SN  - 0040-4020
VL  - 68
IS  - 31
SP  - 6284
EP  - 6288
PB  - PERGAMON-ELSEVIER SCIENCE LTD
CY  - OXFORD
ER  -