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Synthesis and conformational analysis of new naphth[1,2-e][1,3]oxazino[3,4-c]quinazoline derivatives

  • 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.

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Metadaten
Author:Renata Csuetoertoeki, Istvan Szatmari, Andreas Koch, Matthias Heydenreich, Erich Kleinpeter, Ferenc Fueloep
DOI:https://doi.org/10.1016/j.tet.2011.08.074
ISSN:0040-4020 (print)
Parent Title (English):Tetrahedron
Publisher:Elsevier
Place of publication:Oxford
Document Type:Article
Language:English
Year of first Publication:2011
Year of Completion:2011
Release Date:2017/03/26
Tag:Conformational analysis; DFT calculations; Hammett-Brown plots; NMR; Naphthoxazinoquinazolines
Volume:67
Issue:44
Pagenumber:8
First Page:8564
Last Page:8571
Funder:Hungarian Research Foundation (OTKA) [K-75433]; Deutscher Akademischer Austauschdienst (DAAD) [50368559]; Bolyai Janos Fellowship; [TAMOP-4.2.1/B-09/1/KONV-2010-0005]
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer Review:Referiert