Novel piperidine-fused benzoxazino- and quinazolinonaphthoxazines - Synthesis and conformational study

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

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

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, G tct 1 for 4 and G tct 1 for 7, were corroborated by spatial NOE information relating to the H 7a-H 10a-H 15b 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.

Original languageEnglish
Pages (from-to)6284-6288
Number of pages5
JournalTetrahedron
Volume68
Issue number31
DOIs
Publication statusPublished - Aug 5 2012

Keywords

  • Conformational analysis
  • DFT structural study
  • NMR spectroscopy
  • Naphthoxazines
  • Quinazolines

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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