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(6aS*,6bS*,11R*,11aR*)-6-(2-Furylmethyl)-5,12-dioxo-5,6,6a,6b,7,11,11a,12-octahydrofuro[3′,2′:5,6]isoindolo[2,1-a]quinazoline-11-carboxylic acid
The title compound, C(23)H(18)N(2)O(6), is the product of an intramolecular thermal cycloaddition within 1-malein-2-[(E)-2-(2-furyl)vinyl]-4-oxo-3,4-dihydroquinazoline. The molecule comprises a previously unknown fused pentacyclic system containing two five-membered rings (2-pyrrolidinone and...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2011
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3247426/ https://www.ncbi.nlm.nih.gov/pubmed/22220044 http://dx.doi.org/10.1107/S160053681104311X |
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author | Obushak, Mykola D. Horak, Yuri I. Zaytsev, Vladimir P. Motorygina, Ekaterina L. Zubkov, Fedor I. Khrustalev, Victor N. |
author_facet | Obushak, Mykola D. Horak, Yuri I. Zaytsev, Vladimir P. Motorygina, Ekaterina L. Zubkov, Fedor I. Khrustalev, Victor N. |
author_sort | Obushak, Mykola D. |
collection | PubMed |
description | The title compound, C(23)H(18)N(2)O(6), is the product of an intramolecular thermal cycloaddition within 1-malein-2-[(E)-2-(2-furyl)vinyl]-4-oxo-3,4-dihydroquinazoline. The molecule comprises a previously unknown fused pentacyclic system containing two five-membered rings (2-pyrrolidinone and furan) and three six-membered rings (benzene, 2,3-dihydro-4-pyrimidinone and dihydrocyclohexane). The central five-membered pyrrolidinone ring has the usual envelope conformation. The six-membered dihydropyrimidinone and dihydrocyclohexane rings adopt a half-boat and a half-chair conformation, respectively. The dihedral angle between the planes of the terminal benzene and furan rings is 45.99 (7)°. In the crystal, O—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers. Weak C—H⋯O hydrogen bonds consolidate further the crystal packing, which exhibits π–π interactions, with a short distance of 3.556 (3) Å between the centroids of benzene rings of neighbouring molecules. |
format | Online Article Text |
id | pubmed-3247426 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2011 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-32474262012-01-04 (6aS*,6bS*,11R*,11aR*)-6-(2-Furylmethyl)-5,12-dioxo-5,6,6a,6b,7,11,11a,12-octahydrofuro[3′,2′:5,6]isoindolo[2,1-a]quinazoline-11-carboxylic acid Obushak, Mykola D. Horak, Yuri I. Zaytsev, Vladimir P. Motorygina, Ekaterina L. Zubkov, Fedor I. Khrustalev, Victor N. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(23)H(18)N(2)O(6), is the product of an intramolecular thermal cycloaddition within 1-malein-2-[(E)-2-(2-furyl)vinyl]-4-oxo-3,4-dihydroquinazoline. The molecule comprises a previously unknown fused pentacyclic system containing two five-membered rings (2-pyrrolidinone and furan) and three six-membered rings (benzene, 2,3-dihydro-4-pyrimidinone and dihydrocyclohexane). The central five-membered pyrrolidinone ring has the usual envelope conformation. The six-membered dihydropyrimidinone and dihydrocyclohexane rings adopt a half-boat and a half-chair conformation, respectively. The dihedral angle between the planes of the terminal benzene and furan rings is 45.99 (7)°. In the crystal, O—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers. Weak C—H⋯O hydrogen bonds consolidate further the crystal packing, which exhibits π–π interactions, with a short distance of 3.556 (3) Å between the centroids of benzene rings of neighbouring molecules. International Union of Crystallography 2011-10-29 /pmc/articles/PMC3247426/ /pubmed/22220044 http://dx.doi.org/10.1107/S160053681104311X Text en © Obushak et al. 2011 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. |
spellingShingle | Organic Papers Obushak, Mykola D. Horak, Yuri I. Zaytsev, Vladimir P. Motorygina, Ekaterina L. Zubkov, Fedor I. Khrustalev, Victor N. (6aS*,6bS*,11R*,11aR*)-6-(2-Furylmethyl)-5,12-dioxo-5,6,6a,6b,7,11,11a,12-octahydrofuro[3′,2′:5,6]isoindolo[2,1-a]quinazoline-11-carboxylic acid |
title | (6aS*,6bS*,11R*,11aR*)-6-(2-Furylmethyl)-5,12-dioxo-5,6,6a,6b,7,11,11a,12-octahydrofuro[3′,2′:5,6]isoindolo[2,1-a]quinazoline-11-carboxylic acid |
title_full | (6aS*,6bS*,11R*,11aR*)-6-(2-Furylmethyl)-5,12-dioxo-5,6,6a,6b,7,11,11a,12-octahydrofuro[3′,2′:5,6]isoindolo[2,1-a]quinazoline-11-carboxylic acid |
title_fullStr | (6aS*,6bS*,11R*,11aR*)-6-(2-Furylmethyl)-5,12-dioxo-5,6,6a,6b,7,11,11a,12-octahydrofuro[3′,2′:5,6]isoindolo[2,1-a]quinazoline-11-carboxylic acid |
title_full_unstemmed | (6aS*,6bS*,11R*,11aR*)-6-(2-Furylmethyl)-5,12-dioxo-5,6,6a,6b,7,11,11a,12-octahydrofuro[3′,2′:5,6]isoindolo[2,1-a]quinazoline-11-carboxylic acid |
title_short | (6aS*,6bS*,11R*,11aR*)-6-(2-Furylmethyl)-5,12-dioxo-5,6,6a,6b,7,11,11a,12-octahydrofuro[3′,2′:5,6]isoindolo[2,1-a]quinazoline-11-carboxylic acid |
title_sort | (6as*,6bs*,11r*,11ar*)-6-(2-furylmethyl)-5,12-dioxo-5,6,6a,6b,7,11,11a,12-octahydrofuro[3′,2′:5,6]isoindolo[2,1-a]quinazoline-11-carboxylic acid |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3247426/ https://www.ncbi.nlm.nih.gov/pubmed/22220044 http://dx.doi.org/10.1107/S160053681104311X |
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