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Synthesis and conformational analysis of naphth[1', 2':5,6][1,3]oxazino[3,2-c][1,3]benzoxazine and naphth[1', 2':5,6][1,3]oxazino[3,4-c][1,3]benzoxazine derivatives

  • A new functional group, the hydroxy group, was inserted into a Betti base by reaction with salicylaldehyde, and the naphthoxazine derivatives thus obtained were converted by ring-closure reactions with formaldehyde, acetaldehyde, propionaldehyde or phosgene to the corresponding naphth[1',2':5,6][1,3]oxazino[3,2-c][1,3]benzoxazine derivatives. Further, the conformational analysis of these polycyclic compounds by NMR spectroscopy and an accompanying molecular modelling are reported; especially, both quantitative anisotropic ring current effects of the aromatic moieties in these compounds and steric substituent effects were employed to determine the stereochemistry of the naphthoxazinobenzoxazine derivatives.

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Metadaten
Author:Matthias Heydenreich, Andreas Koch, Sabrina Klod, Istvan Szatmari, Ferenc Fülöp, Erich Kleinpeter
URL:http://www.sciencedirect.com/science/journal/00404020
DOI:https://doi.org/10.1016/j.tet.2006.09.037
ISSN:0040-4020
Document Type:Article
Language:English
Year of first Publication:2006
Year of Completion:2006
Release Date:2017/03/24
Source:Tetrahedron. - ISSN 0040-4020. - 62 (2006), 48, S. 11081 - 11089
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer Review:Referiert