Stereochemical studies 871 1 Part 86/81, G. Stájer, A.E. Szabó, J. Pintye, G. Bernáth and P. Sohár, J. Chem. Soc. Perkin 1, Accepted for publication.saturated heterdcycles 821. Synthesis and steric structure of steredisomeric n-substituted tetrahydro-1,3-oxazines fused with norbornane or norbornene

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Abstract

diendo- and diexo-2-Methylamino and 2-benzylamino-3-hydroxymethylbicyclo [2.2.1]heptanes and the corresponding bicycio [2.2.1] heptenes (5a -d, 7a -d) were synthesized from β-amino acid esters containing the norbornane or norbornene skeleton (3a-d). The aminoalcohols were converted to 5,8- methano -3,1-benzoxazines by reaction with formaldehyde. As established by 1H and 13C NMR spectroscopy, the predominant conformation is endo - boat (B) for the diexo, and exo - boat (E) for the diendo derivatives.

Original languageEnglish
Pages (from-to)5159-5168
Number of pages10
JournalTetrahedron
Volume41
Issue number22
DOIs
Publication statusPublished - 1985

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Norbornanes
Oxazines
Ships
Boats
Publications
Benzoxazines
Heptanes
Skeleton
Formaldehyde
Nuclear magnetic resonance spectroscopy
Conformations
Esters
Magnetic Resonance Spectroscopy
Derivatives
Amino Acids
2-norbornene
oxazine 1

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

@article{66b9d35e90a644f090e9a0cb678672b3,
title = "Stereochemical studies 871 1 Part 86/81, G. St{\'a}jer, A.E. Szab{\'o}, J. Pintye, G. Bern{\'a}th and P. Soh{\'a}r, J. Chem. Soc. Perkin 1, Accepted for publication.saturated heterdcycles 821. Synthesis and steric structure of steredisomeric n-substituted tetrahydro-1,3-oxazines fused with norbornane or norbornene",
abstract = "diendo- and diexo-2-Methylamino and 2-benzylamino-3-hydroxymethylbicyclo [2.2.1]heptanes and the corresponding bicycio [2.2.1] heptenes (5a -d, 7a -d) were synthesized from β-amino acid esters containing the norbornane or norbornene skeleton (3a-d). The aminoalcohols were converted to 5,8- methano -3,1-benzoxazines by reaction with formaldehyde. As established by 1H and 13C NMR spectroscopy, the predominant conformation is endo - boat (B) for the diexo, and exo - boat (E) for the diendo derivatives.",
author = "F. F{\"u}l{\"o}p and G. St{\'a}jer and G. Bern{\'a}th and P. Soh{\'a}r",
year = "1985",
doi = "10.1016/S0040-4020(01)96760-2",
language = "English",
volume = "41",
pages = "5159--5168",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "22",

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TY - JOUR

T1 - Stereochemical studies 871 1 Part 86/81, G. Stájer, A.E. Szabó, J. Pintye, G. Bernáth and P. Sohár, J. Chem. Soc. Perkin 1, Accepted for publication.saturated heterdcycles 821. Synthesis and steric structure of steredisomeric n-substituted tetrahydro-1,3-oxazines fused with norbornane or norbornene

AU - Fülöp, F.

AU - Stájer, G.

AU - Bernáth, G.

AU - Sohár, P.

PY - 1985

Y1 - 1985

N2 - diendo- and diexo-2-Methylamino and 2-benzylamino-3-hydroxymethylbicyclo [2.2.1]heptanes and the corresponding bicycio [2.2.1] heptenes (5a -d, 7a -d) were synthesized from β-amino acid esters containing the norbornane or norbornene skeleton (3a-d). The aminoalcohols were converted to 5,8- methano -3,1-benzoxazines by reaction with formaldehyde. As established by 1H and 13C NMR spectroscopy, the predominant conformation is endo - boat (B) for the diexo, and exo - boat (E) for the diendo derivatives.

AB - diendo- and diexo-2-Methylamino and 2-benzylamino-3-hydroxymethylbicyclo [2.2.1]heptanes and the corresponding bicycio [2.2.1] heptenes (5a -d, 7a -d) were synthesized from β-amino acid esters containing the norbornane or norbornene skeleton (3a-d). The aminoalcohols were converted to 5,8- methano -3,1-benzoxazines by reaction with formaldehyde. As established by 1H and 13C NMR spectroscopy, the predominant conformation is endo - boat (B) for the diexo, and exo - boat (E) for the diendo derivatives.

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U2 - 10.1016/S0040-4020(01)96760-2

DO - 10.1016/S0040-4020(01)96760-2

M3 - Article

VL - 41

SP - 5159

EP - 5168

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 22

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