TY  - JOUR
A1  - Barta, Petra
A1  - Szatmari, Istvan
A1  - Fueloep, Ferenc
A1  - Heydenreich, Matthias
A1  - Koch, Andreas
A1  - Kleinpeter, Erich
T1  - Synthesis and stereochemistry of new naphth[1,3]oxazino[3,2-a] benzazepine and naphth[1,3]oxazino[3,2-e]thienopyridine derivatives
JF  - Tetrahedron
N2  - Through the reactions of 1- or 2-naphthol and 4,5-dihydro-3H-benz[c]azepine or 6,7-dihydrothieno[3,2-c]pyridine, new aminonaphthol derivatives were prepared. The syntheses were extended by using N-containing naphthol analogues such as 5-hydroxyisoquinoline and 6-hydroxyquinoline. The ring closures of the novel bifunctional compounds were also achieved, resulting in new naphth[2,1-e][1,3]oxazines, naphth[1,2-e][1,3]oxazines, isoquinolino[5,6-e][1,3]oxazines and quinolino[5,6-e][1,3]oxazines. H-1 NMR spectra of the target heterocycles 16, 20 and 21 were sufficiently resolved to indentify the present stereochemistry; therefore, beside computed structures, spatial experimental (dipolar coupling-NOE) and computed (ring current effect of the naphthyl moiety-TSNMRS) NMR studies were employed. The studied heterocycles exist exclusively as S(14b),R(N), R(14b),S(N), and S(16b)S(N) isomers, respectively. The flexible moieties of the studied compounds prefer. (C) 2016 Elsevier Ltd. All rights reserved.
KW  - Modified Mannich reaction
KW  - Thienopyridine
KW  - Benzazepine
KW  - NMR spectroscopy
KW  - Stereochemistry
KW  - Theoretical calculations
Y1  - 2016
U6  - https://doi.org/10.1016/j.tet.2016.03.058
SN  - 0040-4020
VL  - 72
SP  - 2402
EP  - 2410
PB  - Elsevier
CY  - Oxford
ER  - 
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  -