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Synthesis and conformational analysis of naphthylnaphthoxazine derivatives

  • 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.

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Author:Diána Thóth, István Szatmári, Matthias Heydenreich, Andreas Koch, Erich Kleinpeter, Ferenc Fülöp
Document Type:Article
Year of first Publication:2009
Year of Completion:2009
Release Date:2017/03/25
Source:Journal of molecular structure. - ISSN 0166-1280. - e-ISSN 0022-2860. - 929 (2009), 1-3, S. 58 - 66
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer Review:Referiert