Stereochemical studies - 79 synthesis and kinetic study on the retrodiene decomposition of norbornene-condensed 1,3-oxazin-4-ones

G. Stájer, LászlÓ Mód, Angela E. Szabó, Ferenc Folöp, G. Bernáth, P. Sohár

Research output: Contribution to journalArticle

47 Citations (Scopus)

Abstract

The cis-cxo- amino acid c with norbornene skeleton was converted into 2-aryvl-cis-cxo-1,3-oxazin-4-ones 5a-d. These compounds, similarly to the diendo isomers 1a-d studied by us earlier, undergo retrodiene decomposition under mild conditions to give 2-aryl-62-l,3-oxazin-6-ones (2a-d) in 50-60% yield. The ratio of the decomposition rate constants of the tricyclic diendo and diexo-1,3-oxazin-4-ones, measured in toluene solution, is about 2.

Original languageEnglish
Pages (from-to)2385-2393
Number of pages9
JournalTetrahedron
Volume40
Issue number12
DOIs
Publication statusPublished - 1984

Fingerprint

Toluene
Skeleton
Decomposition
Amino Acids
Kinetics
Isomers
Rate constants
2-norbornene

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Stereochemical studies - 79 synthesis and kinetic study on the retrodiene decomposition of norbornene-condensed 1,3-oxazin-4-ones. / Stájer, G.; Mód, LászlÓ; Szabó, Angela E.; Folöp, Ferenc; Bernáth, G.; Sohár, P.

In: Tetrahedron, Vol. 40, No. 12, 1984, p. 2385-2393.

Research output: Contribution to journalArticle

@article{f2253875dd0d42c081e72055a19e4d72,
title = "Stereochemical studies - 79 synthesis and kinetic study on the retrodiene decomposition of norbornene-condensed 1,3-oxazin-4-ones",
abstract = "The cis-cxo- amino acid c with norbornene skeleton was converted into 2-aryvl-cis-cxo-1,3-oxazin-4-ones 5a-d. These compounds, similarly to the diendo isomers 1a-d studied by us earlier, undergo retrodiene decomposition under mild conditions to give 2-aryl-62-l,3-oxazin-6-ones (2a-d) in 50-60{\%} yield. The ratio of the decomposition rate constants of the tricyclic diendo and diexo-1,3-oxazin-4-ones, measured in toluene solution, is about 2.",
author = "G. St{\'a}jer and L{\'a}szl{\'O} M{\'o}d and Szab{\'o}, {Angela E.} and Ferenc Fol{\"o}p and G. Bern{\'a}th and P. Soh{\'a}r",
year = "1984",
doi = "10.1016/0040-4020(84)80022-8",
language = "English",
volume = "40",
pages = "2385--2393",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "12",

}

TY - JOUR

T1 - Stereochemical studies - 79 synthesis and kinetic study on the retrodiene decomposition of norbornene-condensed 1,3-oxazin-4-ones

AU - Stájer, G.

AU - Mód, LászlÓ

AU - Szabó, Angela E.

AU - Folöp, Ferenc

AU - Bernáth, G.

AU - Sohár, P.

PY - 1984

Y1 - 1984

N2 - The cis-cxo- amino acid c with norbornene skeleton was converted into 2-aryvl-cis-cxo-1,3-oxazin-4-ones 5a-d. These compounds, similarly to the diendo isomers 1a-d studied by us earlier, undergo retrodiene decomposition under mild conditions to give 2-aryl-62-l,3-oxazin-6-ones (2a-d) in 50-60% yield. The ratio of the decomposition rate constants of the tricyclic diendo and diexo-1,3-oxazin-4-ones, measured in toluene solution, is about 2.

AB - The cis-cxo- amino acid c with norbornene skeleton was converted into 2-aryvl-cis-cxo-1,3-oxazin-4-ones 5a-d. These compounds, similarly to the diendo isomers 1a-d studied by us earlier, undergo retrodiene decomposition under mild conditions to give 2-aryl-62-l,3-oxazin-6-ones (2a-d) in 50-60% yield. The ratio of the decomposition rate constants of the tricyclic diendo and diexo-1,3-oxazin-4-ones, measured in toluene solution, is about 2.

UR - http://www.scopus.com/inward/record.url?scp=0000806517&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0000806517&partnerID=8YFLogxK

U2 - 10.1016/0040-4020(84)80022-8

DO - 10.1016/0040-4020(84)80022-8

M3 - Article

AN - SCOPUS:0000806517

VL - 40

SP - 2385

EP - 2393

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 12

ER -