TY  - JOUR
A1  - Thóth, Diána
A1  - Szatmári, István
A1  - Heydenreich, Matthias
A1  - Koch, Andreas
A1  - Kleinpeter, Erich
A1  - Fulop, Ferenc
T1  - Synthesis and conformational analysis of naphthylnaphthoxazine derivatives
N2  - 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.
Y1  - 2009
UR  - https://publishup.uni-potsdam.de/frontdoor/index/index/docId/30799
UR  - http://www.sciencedirect.com/science/journal/00222860
SN  - 0166-1280
ER  -