(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

Mykola D Obushak,Ekaterina L Motorygina,Vladimir P Zaytsev,Yuri I Horak,Fedor I Zubkov,Victor N Khrustalev

doi:10.1107/s160053681104311x

Abstract

The title compound, C23H18N2O6, 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.

Highlights

The title compound, C23H18N2O6, is the product of an intramolecular thermal cycloaddition within 1-malein-2-[(E)2-(2-furyl)vinyl]-4-oxo-3,4-dihydroquinazoline
Within the scope of our investigations on the intramolecular Diels-Alder reaction of furan (IMDAF) (Vogel et al, 1999; Zubkov et al, 2005, 2009, 2010), we demonstrate the possibility of intramolecular thermal cycloaddition within 1-malein-2-[(E)-2-(2furyl)vinyl]-4-oxo-3,4-dihydroquinazoline
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x+1, y, z; (iii) −x+2, −y+1, −z; (iv) x+1/2, −y+3/2, z+1/2; (v) −x+3/2, y+1/2, −z+1/2

Summary

Structure Reports

Khrustalevc a Department of Organic Chemistry, Ivan Franko National University of Lviv, 6 Kyryla i Mefodiya Street, Lviv 79005, Ukraine, bOrganic Chemistry Department, Russian. People’s Friendship University, Miklukho-Maklaya Street 6, Moscow, 117198, Russian Federation, and cX-ray Structural Centre, A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Street, B-334, Moscow 119991, Russian Federation. R factor = 0.060; wR factor = 0.160; data-to-parameter ratio = 18.9

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