Telitett es reszlegesen telitett izoindolo[2,1-a][3,1]benzoxazinok, -[1,2-b][2,4]benzoxazepinonok, ciklopentan- es -hexan[b]pirrolo[2,1-a][3,1]benzoxazin izomerek szintezise

Translated title of the contribution: Preparation and steric structure elucidation of saturated or partially saturated isoindolo[2,1-a]-[3,1]benzoxazinones, -[1,2-b][2,4]benzoxazepinones, cyclopentane- and -cyclohexane[b]pyrrolo[2,1-a][3,1]-benzoxazines

Géza Stájer, Miklós Virág, E. Angela Szabó, Gábor Bernáth, Pál Sohár

Research output: Contribution to journalArticle

Abstract

The reactions of 2-carboxybenzaldehyde with 1,3- or 1,4-aminealcohols were used to prepare partially or fully saturated tetra- and pentacyclic compounds containing a condensed 1,3-oxazino- or oxazepinoisoindolone moiety and one terminal saturated carbocycle. Isoindolol[2,1-a][3,1]-benzoxazinones, stereoisomeric isoindolo[1,2-b][2,4]benzoxazepinones hexahydrocyclopentane[b]pyrrolo[1,2-a][3,1]-benzoxazinone, octahydroindolo[1,2-b]- and decahydroindolo[1,2-a]benzoxazinone and related pentacyclic derivatives were prepared. The diastereomers 5a-c differ in the ring annelation or in the position of the NCHO hydrogens and annelational hydrogens. The stereostructures of these compounds were elucidated by means of 1H and 13C NMR spectroscopy, including DNOE, DEPT, 2D-HSC measurements and X-ray analysis.

Original languageHungarian
Pages (from-to)201-210
Number of pages10
JournalActa Pharmaceutica Hungarica
Volume67
Issue number5
Publication statusPublished - Sep 1997

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Benzoxazines
Cyclopentanes
Hydrogen
Magnetic Resonance Spectroscopy
X-Rays
Cyclohexane

ASJC Scopus subject areas

  • Pharmaceutical Science

Cite this

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title = "Telitett es reszlegesen telitett izoindolo[2,1-a][3,1]benzoxazinok, -[1,2-b][2,4]benzoxazepinonok, ciklopentan- es -hexan[b]pirrolo[2,1-a][3,1]benzoxazin izomerek szintezise",
abstract = "The reactions of 2-carboxybenzaldehyde with 1,3- or 1,4-aminealcohols were used to prepare partially or fully saturated tetra- and pentacyclic compounds containing a condensed 1,3-oxazino- or oxazepinoisoindolone moiety and one terminal saturated carbocycle. Isoindolol[2,1-a][3,1]-benzoxazinones, stereoisomeric isoindolo[1,2-b][2,4]benzoxazepinones hexahydrocyclopentane[b]pyrrolo[1,2-a][3,1]-benzoxazinone, octahydroindolo[1,2-b]- and decahydroindolo[1,2-a]benzoxazinone and related pentacyclic derivatives were prepared. The diastereomers 5a-c differ in the ring annelation or in the position of the NCHO hydrogens and annelational hydrogens. The stereostructures of these compounds were elucidated by means of 1H and 13C NMR spectroscopy, including DNOE, DEPT, 2D-HSC measurements and X-ray analysis.",
author = "G{\'e}za St{\'a}jer and Mikl{\'o}s Vir{\'a}g and Szab{\'o}, {E. Angela} and G{\'a}bor Bern{\'a}th and P{\'a}l Soh{\'a}r",
year = "1997",
month = "9",
language = "Hungarian",
volume = "67",
pages = "201--210",
journal = "Acta Pharmaceutica Hungarica",
issn = "0001-6659",
publisher = "Magyar Gyogyszereszeti Tarsasag",
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AU - Stájer, Géza

AU - Virág, Miklós

AU - Szabó, E. Angela

AU - Bernáth, Gábor

AU - Sohár, Pál

PY - 1997/9

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N2 - The reactions of 2-carboxybenzaldehyde with 1,3- or 1,4-aminealcohols were used to prepare partially or fully saturated tetra- and pentacyclic compounds containing a condensed 1,3-oxazino- or oxazepinoisoindolone moiety and one terminal saturated carbocycle. Isoindolol[2,1-a][3,1]-benzoxazinones, stereoisomeric isoindolo[1,2-b][2,4]benzoxazepinones hexahydrocyclopentane[b]pyrrolo[1,2-a][3,1]-benzoxazinone, octahydroindolo[1,2-b]- and decahydroindolo[1,2-a]benzoxazinone and related pentacyclic derivatives were prepared. The diastereomers 5a-c differ in the ring annelation or in the position of the NCHO hydrogens and annelational hydrogens. The stereostructures of these compounds were elucidated by means of 1H and 13C NMR spectroscopy, including DNOE, DEPT, 2D-HSC measurements and X-ray analysis.

AB - The reactions of 2-carboxybenzaldehyde with 1,3- or 1,4-aminealcohols were used to prepare partially or fully saturated tetra- and pentacyclic compounds containing a condensed 1,3-oxazino- or oxazepinoisoindolone moiety and one terminal saturated carbocycle. Isoindolol[2,1-a][3,1]-benzoxazinones, stereoisomeric isoindolo[1,2-b][2,4]benzoxazepinones hexahydrocyclopentane[b]pyrrolo[1,2-a][3,1]-benzoxazinone, octahydroindolo[1,2-b]- and decahydroindolo[1,2-a]benzoxazinone and related pentacyclic derivatives were prepared. The diastereomers 5a-c differ in the ring annelation or in the position of the NCHO hydrogens and annelational hydrogens. The stereostructures of these compounds were elucidated by means of 1H and 13C NMR spectroscopy, including DNOE, DEPT, 2D-HSC measurements and X-ray analysis.

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