Title of article
Stereochemistry of the methylidene-bridged quinazoline-isoquinoline alkaloid 3-{[6,7-dimethoxy-1-(4-nitrophenyl)-1,2,3,4-tetrahydroisoquinolin-2-yl]methylidene}-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-9-one methanol monosolvate
Author/Authors
Tojiboev, Akmal Laboratory of Thermophysics of Multiphase Systems, Institute of Ion-Plasm and Laser Technologies named after U.A. Arifov - Academy of Sciences of Uzbekistan, Uzbekistan , Zhurakulov, Sherzod S.Yunusov Institute of Chemistry of Plant Substances - Academy of Science of, Uzbekistan, Uzbekistan , Vinogradova, Valentina S.Yunusov Institute of Chemistry of Plant Substances - Academy of Science of, Uzbekistan, Uzbekistan , Englert, Ulli Institute of Inorganic Chemistry - RWTH Aachen University, Aachen, Germany , Wang, Ruimin Institute of Inorganic Chemistry - RWTH Aachen University, Aachen, Germany
Pages
13
From page
1
To page
13
Abstract
Two potentially bioactive fragments, namely a tricyclic quinazoline derivative with an exocyclic alkene moiety and a substituted isoquinoline, are coupled to give 3-{[6,7-dimethoxy-1-(4-nitrophenyl)-1,2,3,4-tetrahydroisoquinolin-2-yl]methylidene}-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-9-one. The target product crystallizes as a methanol solvate, C29H26N4O5·CH4O, and is E configured. The alternative Z isomer would necessarily imply either considerable twist about the central double bond or very unfavourable intramolecular contacts between sterically more demanding substituents. The main residue and the co-crystallized solvent molecule aggregate to discrete pairs via a classical O—H⋯O hydrogen bond with a distance of 2.8581 (7) Å between the methanol OH donor and the quinazolinone O=C acceptor.
Keywords
quinazoline , isoquinoline , steric congestion , hydrogen bonding , crystal structure
Journal title
Acta Crystallographica Section E: Crystallographic Communications
Serial Year
2020
Record number
2623648
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