Stereochemical studies. 81. saturated heterocycles. 69. preparation of methylene-bridged 3,1-benzoxazines, 3,1-benzoxazin-2-ones and 3,1-benzoxazine-2-thiones

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Abstract

3-exo-Aminobicyclo[2.2.1]hept-5-ene-2-exo-carboxylic acid and ethyl 3-endo-aminobicyclo[2.2.1]heptane-2-endo-carboxylate (6) were reduced with lithium aluminum hydride to the corresponding bicyclic aminoalcohols 3 and 4. These and the saturated endo-endo and exo-exo N-methylaminoalcohols 16 and 22, respectively, were converted to methylene-bridged tetrahydro- (11) and hexahydro-3,1-benzoxazin-2-ones 12, 17, 23 and 3,1-benzoxazin-2-thiones 13, 14, 18, 24. The exo-exo 3 and endo-endo 4 aminoalcohols were cyclized by means of ethyl arylimidates to tricyclic dihydro-1,3-oxazines 7a-d, 8a-d. The structures were confirmed by ir, 1H and 13C nmr spectroscopy.

Original languageEnglish
Pages (from-to)1373-1376
Number of pages4
JournalJournal of Heterocyclic Chemistry
Volume21
Issue number5
DOIs
Publication statusPublished - 1984

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Benzoxazines
Oxazines
Thiones
Heptanes
Carboxylic Acids
Spectroscopy
lithium aluminum hydride

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "Stereochemical studies. 81. saturated heterocycles. 69. preparation of methylene-bridged 3,1-benzoxazines, 3,1-benzoxazin-2-ones and 3,1-benzoxazine-2-thiones",
abstract = "3-exo-Aminobicyclo[2.2.1]hept-5-ene-2-exo-carboxylic acid and ethyl 3-endo-aminobicyclo[2.2.1]heptane-2-endo-carboxylate (6) were reduced with lithium aluminum hydride to the corresponding bicyclic aminoalcohols 3 and 4. These and the saturated endo-endo and exo-exo N-methylaminoalcohols 16 and 22, respectively, were converted to methylene-bridged tetrahydro- (11) and hexahydro-3,1-benzoxazin-2-ones 12, 17, 23 and 3,1-benzoxazin-2-thiones 13, 14, 18, 24. The exo-exo 3 and endo-endo 4 aminoalcohols were cyclized by means of ethyl arylimidates to tricyclic dihydro-1,3-oxazines 7a-d, 8a-d. The structures were confirmed by ir, 1H and 13C nmr spectroscopy.",
author = "G. St{\'a}jer and Szab{\~o}, {Angela E.} and F. F{\"u}l{\"o}p and G. Bern{\'a}th and P. Soh{\'a}r",
year = "1984",
doi = "10.1002/jhet.5570210526",
language = "English",
volume = "21",
pages = "1373--1376",
journal = "Journal of Heterocyclic Chemistry",
issn = "0022-152X",
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number = "5",

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TY - JOUR

T1 - Stereochemical studies. 81. saturated heterocycles. 69. preparation of methylene-bridged 3,1-benzoxazines, 3,1-benzoxazin-2-ones and 3,1-benzoxazine-2-thiones

AU - Stájer, G.

AU - Szabõ, Angela E.

AU - Fülöp, F.

AU - Bernáth, G.

AU - Sohár, P.

PY - 1984

Y1 - 1984

N2 - 3-exo-Aminobicyclo[2.2.1]hept-5-ene-2-exo-carboxylic acid and ethyl 3-endo-aminobicyclo[2.2.1]heptane-2-endo-carboxylate (6) were reduced with lithium aluminum hydride to the corresponding bicyclic aminoalcohols 3 and 4. These and the saturated endo-endo and exo-exo N-methylaminoalcohols 16 and 22, respectively, were converted to methylene-bridged tetrahydro- (11) and hexahydro-3,1-benzoxazin-2-ones 12, 17, 23 and 3,1-benzoxazin-2-thiones 13, 14, 18, 24. The exo-exo 3 and endo-endo 4 aminoalcohols were cyclized by means of ethyl arylimidates to tricyclic dihydro-1,3-oxazines 7a-d, 8a-d. The structures were confirmed by ir, 1H and 13C nmr spectroscopy.

AB - 3-exo-Aminobicyclo[2.2.1]hept-5-ene-2-exo-carboxylic acid and ethyl 3-endo-aminobicyclo[2.2.1]heptane-2-endo-carboxylate (6) were reduced with lithium aluminum hydride to the corresponding bicyclic aminoalcohols 3 and 4. These and the saturated endo-endo and exo-exo N-methylaminoalcohols 16 and 22, respectively, were converted to methylene-bridged tetrahydro- (11) and hexahydro-3,1-benzoxazin-2-ones 12, 17, 23 and 3,1-benzoxazin-2-thiones 13, 14, 18, 24. The exo-exo 3 and endo-endo 4 aminoalcohols were cyclized by means of ethyl arylimidates to tricyclic dihydro-1,3-oxazines 7a-d, 8a-d. The structures were confirmed by ir, 1H and 13C nmr spectroscopy.

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U2 - 10.1002/jhet.5570210526

DO - 10.1002/jhet.5570210526

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