Saturated heterocycles 115. Cycloaddition of nitrilimine and nitrile oxide to norbornane- and norbornene-fused dihydro-1,3-oxazines

G. Stájer, Angela E. Szabó, G. Bernáth, P. Sohár

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

By cycloaddition of nitrilimine and nitrile oxide to diexo and diendo norbornane- and norbornene-fused structural isomeric dihydro-1,3-oxazlnes (1-3), tetracyclic 1,3-oxazino-1, 2,4-trlazolines (7-9) and 1,2,4-oxadiazolines (10-12) were obtained. With norbornehe dipolarophiles, which contain a C=N and a C=C bond, the cycloaddition takes place at the olefinic bond and the diexo compound 4 yields 13 regioselectively, whereas the diendo isomer 5 gives an Isomeric mixture of isoxazolines 14 and 15. From the diexo derivative 6, however, a bis-adduct 16 is formed. The stereostructures of the adducts have been elucidated by NMR spectroscopy.

Original languageEnglish
Pages (from-to)1931-1936
Number of pages6
JournalTetrahedron
Volume43
Issue number8
DOIs
Publication statusPublished - 1987

Fingerprint

Norbornanes
Oxazines
Nitriles
Cycloaddition
Cycloaddition Reaction
Oxides
Isomers
Nuclear magnetic resonance spectroscopy
Magnetic Resonance Spectroscopy
Derivatives
2-norbornene
oxazine 1

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

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title = "Saturated heterocycles 115. Cycloaddition of nitrilimine and nitrile oxide to norbornane- and norbornene-fused dihydro-1,3-oxazines",
abstract = "By cycloaddition of nitrilimine and nitrile oxide to diexo and diendo norbornane- and norbornene-fused structural isomeric dihydro-1,3-oxazlnes (1-3), tetracyclic 1,3-oxazino-1, 2,4-trlazolines (7-9) and 1,2,4-oxadiazolines (10-12) were obtained. With norbornehe dipolarophiles, which contain a C=N and a C=C bond, the cycloaddition takes place at the olefinic bond and the diexo compound 4 yields 13 regioselectively, whereas the diendo isomer 5 gives an Isomeric mixture of isoxazolines 14 and 15. From the diexo derivative 6, however, a bis-adduct 16 is formed. The stereostructures of the adducts have been elucidated by NMR spectroscopy.",
author = "G. St{\'a}jer and Szab{\'o}, {Angela E.} and G. Bern{\'a}th and P. Soh{\'a}r",
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TY - JOUR

T1 - Saturated heterocycles 115. Cycloaddition of nitrilimine and nitrile oxide to norbornane- and norbornene-fused dihydro-1,3-oxazines

AU - Stájer, G.

AU - Szabó, Angela E.

AU - Bernáth, G.

AU - Sohár, P.

PY - 1987

Y1 - 1987

N2 - By cycloaddition of nitrilimine and nitrile oxide to diexo and diendo norbornane- and norbornene-fused structural isomeric dihydro-1,3-oxazlnes (1-3), tetracyclic 1,3-oxazino-1, 2,4-trlazolines (7-9) and 1,2,4-oxadiazolines (10-12) were obtained. With norbornehe dipolarophiles, which contain a C=N and a C=C bond, the cycloaddition takes place at the olefinic bond and the diexo compound 4 yields 13 regioselectively, whereas the diendo isomer 5 gives an Isomeric mixture of isoxazolines 14 and 15. From the diexo derivative 6, however, a bis-adduct 16 is formed. The stereostructures of the adducts have been elucidated by NMR spectroscopy.

AB - By cycloaddition of nitrilimine and nitrile oxide to diexo and diendo norbornane- and norbornene-fused structural isomeric dihydro-1,3-oxazlnes (1-3), tetracyclic 1,3-oxazino-1, 2,4-trlazolines (7-9) and 1,2,4-oxadiazolines (10-12) were obtained. With norbornehe dipolarophiles, which contain a C=N and a C=C bond, the cycloaddition takes place at the olefinic bond and the diexo compound 4 yields 13 regioselectively, whereas the diendo isomer 5 gives an Isomeric mixture of isoxazolines 14 and 15. From the diexo derivative 6, however, a bis-adduct 16 is formed. The stereostructures of the adducts have been elucidated by NMR spectroscopy.

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