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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 benzoxazinonaphthoxazine 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, Gtct1 for 4 and Gtct1 for 7, were corroborated by spatial NOE information relating to the H7a-H10a-H15b 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.

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Author:Erich Kleinpeter, Renáta Csütörtöki, Iván Szatmári, Matthias Heydenreich, Andreas Koch, Ines Starke, Ferenc Fülop
Document Type:Article
Year of first Publication:2012
Year of Completion:2012
Release Date:2017/03/25
Source:Tetrahedron. - ISSN 0040-4020. - 68 (2012), 31, S. 6284 - 6288
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie