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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.
Author details: | Renata Csuetoertoeki, Istvan SzatmariORCiD, Andreas KochORCiDGND, Matthias HeydenreichORCiD, Erich KleinpeterORCiDGND, Ferenc Fueloep |
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DOI: | https://doi.org/10.1016/j.tet.2011.08.074 |
ISSN: | 0040-4020 |
Title of parent work (English): | Tetrahedron |
Publisher: | Elsevier |
Place of publishing: | Oxford |
Publication type: | Article |
Language: | English |
Year of first publication: | 2011 |
Publication year: | 2011 |
Release date: | 2017/03/26 |
Tag: | Conformational analysis; DFT calculations; Hammett-Brown plots; NMR; Naphthoxazinoquinazolines |
Volume: | 67 |
Issue: | 44 |
Number of pages: | 8 |
First page: | 8564 |
Last Page: | 8571 |
Funding institution: | 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 |