Stereochemical studies, 58, saturated heterocycles, 39 [1]. Preparation and steric structures of dihydro-1,3-oxazines, 1,3-oxazin-2-ones and 1,3-oxazine-2-thiones fused with norbornane and norbornene

G. Stájer, E. A. Szabo, F. Fülöp

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Abstract

3-endo-Aminobicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid(1), prepared from endo-norborn-5-ene-2,3-dicarboxylic acid anhydride, and the analogous saturated cis-exo-amino acid (3) were reduced with lithium aluminum hydride to the aminoalcohols 2 and 4; the latter were cyclized by means of arylimino ethers to methylene-bridged tetrahydro-(6a-e) and hexahydro-3,1-benzoxazines (7b-d), respectively. The endo (2) and exo (4) aminoalcohols were converted to methylene-bridged tetrahydro-3,1-benzoxazin-2-one (9) and hexahydro-3,1-benzoxazin-2-one (12) with ethyl chloroformate and sodium methoxide; treatment of the alcohols with carbon disulfide gave, via the dithiocarbamates, the corresponding 2-thiones (11, 13). The structures were confirmed by ir and nmr specroscopy.

Original languageEnglish
Pages (from-to)1181-1185
Number of pages5
JournalJournal of Heterocyclic Chemistry
Volume20
Issue number5
Publication statusPublished - 1983

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Norbornanes
Benzoxazines
Oxazines
Carbon Disulfide
Thiones
Dicarboxylic Acids
Ethers
Anhydrides
Carboxylic Acids
Methanol
Alcohols
Amino Acids
2-norbornene
oxazine 1
lithium aluminum hydride
ethyl chloroformate

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "Stereochemical studies, 58, saturated heterocycles, 39 [1]. Preparation and steric structures of dihydro-1,3-oxazines, 1,3-oxazin-2-ones and 1,3-oxazine-2-thiones fused with norbornane and norbornene",
abstract = "3-endo-Aminobicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid(1), prepared from endo-norborn-5-ene-2,3-dicarboxylic acid anhydride, and the analogous saturated cis-exo-amino acid (3) were reduced with lithium aluminum hydride to the aminoalcohols 2 and 4; the latter were cyclized by means of arylimino ethers to methylene-bridged tetrahydro-(6a-e) and hexahydro-3,1-benzoxazines (7b-d), respectively. The endo (2) and exo (4) aminoalcohols were converted to methylene-bridged tetrahydro-3,1-benzoxazin-2-one (9) and hexahydro-3,1-benzoxazin-2-one (12) with ethyl chloroformate and sodium methoxide; treatment of the alcohols with carbon disulfide gave, via the dithiocarbamates, the corresponding 2-thiones (11, 13). The structures were confirmed by ir and nmr specroscopy.",
author = "G. St{\'a}jer and Szabo, {E. A.} and F. F{\"u}l{\"o}p",
year = "1983",
language = "English",
volume = "20",
pages = "1181--1185",
journal = "Journal of Heterocyclic Chemistry",
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T1 - Stereochemical studies, 58, saturated heterocycles, 39 [1]. Preparation and steric structures of dihydro-1,3-oxazines, 1,3-oxazin-2-ones and 1,3-oxazine-2-thiones fused with norbornane and norbornene

AU - Stájer, G.

AU - Szabo, E. A.

AU - Fülöp, F.

PY - 1983

Y1 - 1983

N2 - 3-endo-Aminobicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid(1), prepared from endo-norborn-5-ene-2,3-dicarboxylic acid anhydride, and the analogous saturated cis-exo-amino acid (3) were reduced with lithium aluminum hydride to the aminoalcohols 2 and 4; the latter were cyclized by means of arylimino ethers to methylene-bridged tetrahydro-(6a-e) and hexahydro-3,1-benzoxazines (7b-d), respectively. The endo (2) and exo (4) aminoalcohols were converted to methylene-bridged tetrahydro-3,1-benzoxazin-2-one (9) and hexahydro-3,1-benzoxazin-2-one (12) with ethyl chloroformate and sodium methoxide; treatment of the alcohols with carbon disulfide gave, via the dithiocarbamates, the corresponding 2-thiones (11, 13). The structures were confirmed by ir and nmr specroscopy.

AB - 3-endo-Aminobicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid(1), prepared from endo-norborn-5-ene-2,3-dicarboxylic acid anhydride, and the analogous saturated cis-exo-amino acid (3) were reduced with lithium aluminum hydride to the aminoalcohols 2 and 4; the latter were cyclized by means of arylimino ethers to methylene-bridged tetrahydro-(6a-e) and hexahydro-3,1-benzoxazines (7b-d), respectively. The endo (2) and exo (4) aminoalcohols were converted to methylene-bridged tetrahydro-3,1-benzoxazin-2-one (9) and hexahydro-3,1-benzoxazin-2-one (12) with ethyl chloroformate and sodium methoxide; treatment of the alcohols with carbon disulfide gave, via the dithiocarbamates, the corresponding 2-thiones (11, 13). The structures were confirmed by ir and nmr specroscopy.

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