Synthesis and conformational analysis of naphth[1,2-e][1,3]oxazino[4,3-a][1,3]isoquinoline and naphth[2,1-e][1,3]oxazino[4,3-a]isoquinoline derivatives

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

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Through the cyclization of 1-(β-hydroxynaphthyl)-1,2,3,4-tetrahydroisoquinoline and 1-(α-hydroxynaphthyl)-1,2,3,4-tetrahydroisoquinoline with formaldehyde, phosgene, p-nitrobenzaldehyde or p-chlorophenyl isothiocyanate, 8-substituted 10,11-dihydro-8H,15bH-naphth[1,2-e][1,3]oxazino[4,3-a]isoquinolines (3 and 4) and 10,11-dihydro-8H,15bH-naphth[2,1-e][1,3]oxazino[4,3-a]isoquinolines (15 and 16) were prepared. Conformational analysis of both the piperidine and the 1,3-oxazine moieties of these heterocycles by NMR spectroscopy and an accompanying theoretical study revealed that these two conformationally flexible six-membered ring moieties prefer twisted chair conformers.

Original languageEnglish
Pages (from-to)7378-7385
Number of pages8
JournalTetrahedron
Volume64
Issue number30-31
DOIs
Publication statusPublished - Jul 21 2008

Fingerprint

Isoquinolines
Phosgene
Oxazines
Derivatives
Cyclization
Formaldehyde
Nuclear magnetic resonance spectroscopy
Theoretical Models
Magnetic Resonance Spectroscopy
isoquinoline
1,2,3,4-tetrahydroisoquinoline

Keywords

  • Conformational analysis
  • Isoquinolines
  • Naphthoxazines
  • NMR spectroscopy
  • Synthesis
  • Theoretical calculations

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis and conformational analysis of naphth[1,2-e][1,3]oxazino[4,3-a][1,3]isoquinoline and naphth[2,1-e][1,3]oxazino[4,3-a]isoquinoline derivatives. / Heydenreich, Matthias; Koch, Andreas; Szatmári, I.; Fülöp, F.; Kleinpeter, Erich.

In: Tetrahedron, Vol. 64, No. 30-31, 21.07.2008, p. 7378-7385.

Research output: Contribution to journalArticle

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