Preparation and steric structure of partially saturated isoindolo[1,3]‐ and ‐[3,1]benzoxazinones and ‐[2,4]benzoxazepinones

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Abstract

From cis‐2‐(p‐methylbenzoyl)cyclohexanecarboxylic acid (1), diendo‐3‐(p‐methylbenzoyl)bicyclo[2.2.1]heptane‐2‐carboxylic acid (2) or 2‐(p‐methylbenzoyl)benzoic acid (3) with stereoisomeric 1,3‐ or 1,4‐amino alcohols with cyclohexane/ene or norbornane/ene skeletons, various partially or fully saturated isoindolo[1,2‐b] [1,3]‐ and ‐[2,1‐a] [3,1]benzoxazinones methylene‐bridged derivatives and [1,2‐c] [2,4]benzoxazepinones were prepared. For these compounds, containing two hetero rings and two or three cycloalkane rings, the stereostructures (the annelation of the terminal rings and aryl group) were established by 1H and 13C NMR spectroscopy, including DNOE, DEPT and 2D‐HSC measurements.

Original languageEnglish
Pages (from-to)329-336
Number of pages8
JournalMagnetic Resonance in Chemistry
Volume33
Issue number5
DOIs
Publication statusPublished - 1995

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Norbornanes
Benzoxazines
Cycloparaffins
Benzoic Acid
Nuclear magnetic resonance spectroscopy
Alcohols
Derivatives
Acids
Benzoic acid
Cyclohexane
cyclohexanecarboxylic acid

Keywords

  • C NMR
  • H NMR
  • 2D‐HSC
  • benzoxazepinones
  • benzoxazinones
  • configuration
  • conformation
  • NMR
  • NOE

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Science(all)

Cite this

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title = "Preparation and steric structure of partially saturated isoindolo[1,3]‐ and ‐[3,1]benzoxazinones and ‐[2,4]benzoxazepinones",
abstract = "From cis‐2‐(p‐methylbenzoyl)cyclohexanecarboxylic acid (1), diendo‐3‐(p‐methylbenzoyl)bicyclo[2.2.1]heptane‐2‐carboxylic acid (2) or 2‐(p‐methylbenzoyl)benzoic acid (3) with stereoisomeric 1,3‐ or 1,4‐amino alcohols with cyclohexane/ene or norbornane/ene skeletons, various partially or fully saturated isoindolo[1,2‐b] [1,3]‐ and ‐[2,1‐a] [3,1]benzoxazinones methylene‐bridged derivatives and [1,2‐c] [2,4]benzoxazepinones were prepared. For these compounds, containing two hetero rings and two or three cycloalkane rings, the stereostructures (the annelation of the terminal rings and aryl group) were established by 1H and 13C NMR spectroscopy, including DNOE, DEPT and 2D‐HSC measurements.",
keywords = "C NMR, H NMR, 2D‐HSC, benzoxazepinones, benzoxazinones, configuration, conformation, NMR, NOE",
author = "P{\'a}l Soh{\'a}r and G{\'e}za St{\'a}jer and Katalin Nagy and G{\'a}bor Bern{\'a}th",
year = "1995",
doi = "10.1002/mrc.1260330503",
language = "English",
volume = "33",
pages = "329--336",
journal = "Magnetic Resonance in Chemistry",
issn = "0749-1581",
publisher = "John Wiley and Sons Ltd",
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T1 - Preparation and steric structure of partially saturated isoindolo[1,3]‐ and ‐[3,1]benzoxazinones and ‐[2,4]benzoxazepinones

AU - Sohár, Pál

AU - Stájer, Géza

AU - Nagy, Katalin

AU - Bernáth, Gábor

PY - 1995

Y1 - 1995

N2 - From cis‐2‐(p‐methylbenzoyl)cyclohexanecarboxylic acid (1), diendo‐3‐(p‐methylbenzoyl)bicyclo[2.2.1]heptane‐2‐carboxylic acid (2) or 2‐(p‐methylbenzoyl)benzoic acid (3) with stereoisomeric 1,3‐ or 1,4‐amino alcohols with cyclohexane/ene or norbornane/ene skeletons, various partially or fully saturated isoindolo[1,2‐b] [1,3]‐ and ‐[2,1‐a] [3,1]benzoxazinones methylene‐bridged derivatives and [1,2‐c] [2,4]benzoxazepinones were prepared. For these compounds, containing two hetero rings and two or three cycloalkane rings, the stereostructures (the annelation of the terminal rings and aryl group) were established by 1H and 13C NMR spectroscopy, including DNOE, DEPT and 2D‐HSC measurements.

AB - From cis‐2‐(p‐methylbenzoyl)cyclohexanecarboxylic acid (1), diendo‐3‐(p‐methylbenzoyl)bicyclo[2.2.1]heptane‐2‐carboxylic acid (2) or 2‐(p‐methylbenzoyl)benzoic acid (3) with stereoisomeric 1,3‐ or 1,4‐amino alcohols with cyclohexane/ene or norbornane/ene skeletons, various partially or fully saturated isoindolo[1,2‐b] [1,3]‐ and ‐[2,1‐a] [3,1]benzoxazinones methylene‐bridged derivatives and [1,2‐c] [2,4]benzoxazepinones were prepared. For these compounds, containing two hetero rings and two or three cycloalkane rings, the stereostructures (the annelation of the terminal rings and aryl group) were established by 1H and 13C NMR spectroscopy, including DNOE, DEPT and 2D‐HSC measurements.

KW - C NMR

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KW - 2D‐HSC

KW - benzoxazepinones

KW - benzoxazinones

KW - configuration

KW - conformation

KW - NMR

KW - NOE

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