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

Renáta Csütörtöki, István Szatmári, Andreas Koch, Matthias Heydenreich, Erich Kleinpeter, Ferenc Fülöp

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)8564-8571
Number of pages8
JournalTetrahedron
Volume67
Issue number44
DOIs
Publication statusPublished - Nov 4 2011

Keywords

  • Conformational analysis
  • DFT calculations
  • Hammett-Brown plots
  • NMR
  • Naphthoxazinoquinazolines

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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