@article{BartaSzatmariFueloepetal.2016, author = {Barta, Petra and Szatmari, Istvan and Fueloep, Ferenc and Heydenreich, Matthias and Koch, Andreas and Kleinpeter, Erich}, title = {Synthesis and stereochemistry of new naphth[1,3]oxazino[3,2-a] benzazepine and naphth[1,3]oxazino[3,2-e]thienopyridine derivatives}, series = {Tetrahedron}, volume = {72}, journal = {Tetrahedron}, publisher = {Elsevier}, address = {Oxford}, issn = {0040-4020}, doi = {10.1016/j.tet.2016.03.058}, pages = {2402 -- 2410}, year = {2016}, abstract = {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.}, language = {en} } @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} } @article{CsuetoertoekiSzatmariKochetal.2011, author = {Csuetoertoeki, Renata and Szatmari, Istvan and Koch, Andreas and Heydenreich, Matthias and Kleinpeter, Erich and Fueloep, Ferenc}, title = {Synthesis and conformational analysis of new naphth[1,2-e][1,3]oxazino[3,4-c]quinazoline derivatives}, series = {Tetrahedron}, volume = {67}, journal = {Tetrahedron}, number = {44}, publisher = {Elsevier}, address = {Oxford}, issn = {0040-4020}, doi = {10.1016/j.tet.2011.08.074}, pages = {8564 -- 8571}, year = {2011}, abstract = {A new highly functionalized aminonaphthol derivative, 1-(amino(2-aminophenyl)methyl)-2-naphthol (4), was synthesized by the reaction of 2-naphthol, 2-nitrobenzaldehyde and tert-butyl carbamate or benzyl carbamate, followed by reduction and/or removal of the protecting group. The aminonaphthol derivative thus obtained was converted in ring-closure reactions with formaldehyde. benzaldehyde and/or phosgene to the corresponding naphth[1,2-e][1,3]oxazino[3,4-c]quinazoline derivatives. The conformational analysis of some derivatives by NMR spectroscopy and accompanying molecular modelling are also reported.}, language = {en} }