Synthesis and stereochemistry of new naphth[1,3]oxazino[3,2-a]benzazepine and naphth[1,3]oxazino[3,2-e]thienopyridine derivatives

Petra Barta, István Szatmári, Ferenc Fülöp, Matthias Heydenreich, Andreas Koch, Erich Kleinpeter

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Through the reactions of 1- or 2-naphthol and 4,5-dihydro-3H-benz[c]azepine or 6,7-dihydrothieno[3,2-c]pyridine, new aminonaphthol derivatives were prepared. The syntheses were extended by using N-containing naphthol analogues such as 5-hydroxyisoquinoline and 6-hydroxyquinoline. The ring closures of the novel bifunctional compounds were also achieved, resulting in new naphth[2,1-e][1,3]oxazines, naphth[1,2-e][1,3]oxazines, isoquinolino[5,6-e][1,3]oxazines and quinolino[5,6-e][1,3]oxazines. 1H NMR spectra of the target heterocycles 16, 20 and 21 were sufficiently resolved to indentify the present stereochemistry; therefore, beside computed structures, spatial experimental (dipolar coupling-NOE) and computed (ring current effect of the naphthyl moiety-TSNMRS) NMR studies were employed. The studied heterocycles exist exclusively as S(14b),R(N), R(14b),S(N), and S(16b)S(N) isomers, respectively. The flexible moieties of the studied compounds prefer.

Original languageEnglish
Pages (from-to)2402-2410
Number of pages9
JournalTetrahedron
Volume72
Issue number19
DOIs
Publication statusPublished - May 12 2016

Keywords

  • Benzazepine
  • Modified Mannich reaction
  • NMR spectroscopy
  • Stereochemistry
  • Theoretical calculations
  • Thienopyridine

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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