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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.

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Author:Renata Csuetoertoeki, Istvan Szatmari, Matthias Heydenreich, Andreas Koch, Ines Starke, Ferenc Fueloep, Erich Kleinpeter
ISSN:0040-4020 (print)
Parent Title (English):TETRAHEDRON
Place of publication:OXFORD
Document Type:Article
Year of first Publication:2012
Year of Completion:2012
Release Date:2017/03/26
Tag:Conformational analysis; DFT structural study; NMR spectroscopy; Naphthoxazines; Quinazolines
First Page:6284
Last Page:6288
Funder:Hungarian Research Foundation (OTKA) [K-75433, TAMOP-4.2.1/B-09/KONV-2010-0005]; Deutsche Akademische Austauschdienst (DAAD) [50368559]; Bolyai Janos Fellowship