Synthesis and conformational analysis of naphthylnaphthoxazine derivatives

Diána Tóth, I. Szatmári, Matthias Heydenreich, Andreas Koch, Erich Kleinpeter, F. Fülöp

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Four new primary aminonaphthols (4, 5, 9 and 10) were synthesized from 1- or 2-naphthol and 1- or 2-naphthaldehyde via naphthoxazines in modified Mannich condensations. Simple ring-closure reactions of these aminonaphthols with paraformaldehyde, 4-nitrobenzaldehyde, phosgene or 4-chlorophenyl isothiocyanate led to new heterocyclic derivatives. In these transformations, either an sp2 or an sp3 carbon was inserted between the hydroxy and amino groups. The effects of substituents and the naphthyl ring on the conformation were investigated by means of NMR measurements, employing both dipolar and scalar couplings. The structures were confirmed by DFT quantum chemical calculations involving computed coupling constants, intramolecular distances between nuclei and the relative energies of the preferred conformers.

Original languageEnglish
Pages (from-to)58-66
Number of pages9
JournalJournal of Molecular Structure
Volume929
Issue number1-3
DOIs
Publication statusPublished - Jul 16 2009

Fingerprint

4-nitrobenzaldehyde
Phosgene
Discrete Fourier transforms
Conformations
Condensation
Carbon
Nuclear magnetic resonance
Derivatives
2-naphthol
1-naphthaldehyde
1-naphthol
paraform
2-naphthaldehyde
1-chloro-4-isothiocyanatobenzene

Keywords

  • Aminonaphthols
  • Conformational analysis
  • DFT calculations
  • Naphthoxazines
  • NBO analysis

ASJC Scopus subject areas

  • Spectroscopy
  • Analytical Chemistry
  • Inorganic Chemistry
  • Organic Chemistry

Cite this

Synthesis and conformational analysis of naphthylnaphthoxazine derivatives. / Tóth, Diána; Szatmári, I.; Heydenreich, Matthias; Koch, Andreas; Kleinpeter, Erich; Fülöp, F.

In: Journal of Molecular Structure, Vol. 929, No. 1-3, 16.07.2009, p. 58-66.

Research output: Contribution to journalArticle

Tóth, Diána ; Szatmári, I. ; Heydenreich, Matthias ; Koch, Andreas ; Kleinpeter, Erich ; Fülöp, F. / Synthesis and conformational analysis of naphthylnaphthoxazine derivatives. In: Journal of Molecular Structure. 2009 ; Vol. 929, No. 1-3. pp. 58-66.
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