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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...

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Autores principales: Obushak, Mykola D., Horak, Yuri I., Zaytsev, Vladimir P., Motorygina, Ekaterina L., Zubkov, Fedor I., Khrustalev, Victor N.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2011
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.
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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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