Preparation of diastereomeric 5,8‐methanobenzoxazino[2,1–6]‐ and [2,3–6]‐1,3‐benzoxazin‐4‐ones by reaction of norbornane/ene‐condensed dihydro‐1,3‐oxazines with salicyl chloride

G. Stájer, Samuel Frimpong‐Manso, G. Bernáth, P. Sohár

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Norbornane and norbornene‐condensed dihydro‐1,3‐oxazines 1–6 were converted with salicyl chloride to 5,8‐methanobenzoxazino[2,1–6]‐ and ‐[2,3‐b]‐1,3‐benzoxazin‐4‐ones 7–12. The addition takes place to the C  N bond: after acylation, the intermediate is stabilized through cyclization to the aryl‐substituted carbon by hydrogen chloride elimination. Diastereomers containing the oxazine rings in isomeric positions could be isolated in two cases. This is the first example of the isolation of diastereomers in such a salicyl chloride reaction. In contrast with earlier findings with reactions of related systems, no addition to the C  C bond could be observed. The steric structures of the compounds were elucidated by ir, 1H‐ and 13C‐nmr spectroscopy.

Original languageEnglish
Pages (from-to)753-757
Number of pages5
JournalJournal of Heterocyclic Chemistry
Volume28
Issue number3
DOIs
Publication statusPublished - 1991

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Norbornanes
Chlorides
Oxazines
Acylation
Hydrochloric Acid
Cyclization
Carbon
Spectroscopy

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "Preparation of diastereomeric 5,8‐methanobenzoxazino[2,1–6]‐ and [2,3–6]‐1,3‐benzoxazin‐4‐ones by reaction of norbornane/ene‐condensed dihydro‐1,3‐oxazines with salicyl chloride",
abstract = "Norbornane and norbornene‐condensed dihydro‐1,3‐oxazines 1–6 were converted with salicyl chloride to 5,8‐methanobenzoxazino[2,1–6]‐ and ‐[2,3‐b]‐1,3‐benzoxazin‐4‐ones 7–12. The addition takes place to the C  N bond: after acylation, the intermediate is stabilized through cyclization to the aryl‐substituted carbon by hydrogen chloride elimination. Diastereomers containing the oxazine rings in isomeric positions could be isolated in two cases. This is the first example of the isolation of diastereomers in such a salicyl chloride reaction. In contrast with earlier findings with reactions of related systems, no addition to the C  C bond could be observed. The steric structures of the compounds were elucidated by ir, 1H‐ and 13C‐nmr spectroscopy.",
author = "G. St{\'a}jer and Samuel Frimpong‐Manso and G. Bern{\'a}th and P. Soh{\'a}r",
year = "1991",
doi = "10.1002/jhet.5570280334",
language = "English",
volume = "28",
pages = "753--757",
journal = "Journal of Heterocyclic Chemistry",
issn = "0022-152X",
publisher = "Heterocorporation",
number = "3",

}

TY - JOUR

T1 - Preparation of diastereomeric 5,8‐methanobenzoxazino[2,1–6]‐ and [2,3–6]‐1,3‐benzoxazin‐4‐ones by reaction of norbornane/ene‐condensed dihydro‐1,3‐oxazines with salicyl chloride

AU - Stájer, G.

AU - Frimpong‐Manso, Samuel

AU - Bernáth, G.

AU - Sohár, P.

PY - 1991

Y1 - 1991

N2 - Norbornane and norbornene‐condensed dihydro‐1,3‐oxazines 1–6 were converted with salicyl chloride to 5,8‐methanobenzoxazino[2,1–6]‐ and ‐[2,3‐b]‐1,3‐benzoxazin‐4‐ones 7–12. The addition takes place to the C  N bond: after acylation, the intermediate is stabilized through cyclization to the aryl‐substituted carbon by hydrogen chloride elimination. Diastereomers containing the oxazine rings in isomeric positions could be isolated in two cases. This is the first example of the isolation of diastereomers in such a salicyl chloride reaction. In contrast with earlier findings with reactions of related systems, no addition to the C  C bond could be observed. The steric structures of the compounds were elucidated by ir, 1H‐ and 13C‐nmr spectroscopy.

AB - Norbornane and norbornene‐condensed dihydro‐1,3‐oxazines 1–6 were converted with salicyl chloride to 5,8‐methanobenzoxazino[2,1–6]‐ and ‐[2,3‐b]‐1,3‐benzoxazin‐4‐ones 7–12. The addition takes place to the C  N bond: after acylation, the intermediate is stabilized through cyclization to the aryl‐substituted carbon by hydrogen chloride elimination. Diastereomers containing the oxazine rings in isomeric positions could be isolated in two cases. This is the first example of the isolation of diastereomers in such a salicyl chloride reaction. In contrast with earlier findings with reactions of related systems, no addition to the C  C bond could be observed. The steric structures of the compounds were elucidated by ir, 1H‐ and 13C‐nmr spectroscopy.

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U2 - 10.1002/jhet.5570280334

DO - 10.1002/jhet.5570280334

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VL - 28

SP - 753

EP - 757

JO - Journal of Heterocyclic Chemistry

JF - Journal of Heterocyclic Chemistry

SN - 0022-152X

IS - 3

ER -