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Novel piperidine-fused benzoxazino- and quinazolinonaphthoxazines-synthesis and conformational study
- 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.
Verfasserangaben: | Renata Csuetoertoeki, Istvan SzatmariORCiD, Matthias HeydenreichORCiD, Andreas KochORCiDGND, Ines StarkeORCiD, Ferenc Fueloep, Erich KleinpeterORCiDGND |
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DOI: | https://doi.org/10.1016/j.tet.2012.05.048 |
ISSN: | 0040-4020 |
Titel des übergeordneten Werks (Englisch): | TETRAHEDRON |
Verlag: | PERGAMON-ELSEVIER SCIENCE LTD |
Verlagsort: | OXFORD |
Publikationstyp: | Wissenschaftlicher Artikel |
Sprache: | Englisch |
Jahr der Erstveröffentlichung: | 2012 |
Erscheinungsjahr: | 2012 |
Datum der Freischaltung: | 26.03.2017 |
Freies Schlagwort / Tag: | Conformational analysis; DFT structural study; NMR spectroscopy; Naphthoxazines; Quinazolines |
Band: | 68 |
Ausgabe: | 31 |
Seitenanzahl: | 5 |
Erste Seite: | 6284 |
Letzte Seite: | 6288 |
Fördernde Institution: | Hungarian Research Foundation (OTKA) [K-75433, TAMOP-4.2.1/B-09/KONV-2010-0005]; Deutsche Akademische Austauschdienst (DAAD) [50368559]; Bolyai Janos Fellowship |