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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

Akmal TojiboevLaboratory of Thermophysics of Multiphase Systems , Institute of Ion-Plasm and Laser Technologies named after U.A. Arifov , Academy of Sciences of Uzbekistan , 100125 , Durmon yuli st. 33 , Tashkent , Uzbekistan ,Sherzod ZhurakulovS Валентина ВиноградоваS Ulli EnglertYunusov Institute of Chemistry of Plant Substances , Academy of Science of , Uzbekistan , Mirzo Ulugbek Str. 77 , 100170 Tashkent , Uzbekistan , andRuimin WangYunusov Institute of Chemistry of Plant Substances , Academy of Science of , Uzbekistan , Mirzo Ulugbek Str. 77 , 100170 Tashkent , Uzbekistan , and
2020en
ABI

Annotatsiya

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, C 29 H 26 N 4 O 5 ÁCH 4 O, 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-HÁ Á ÁO hydrogen bond with a distance of 2.8581 (7) A ˚between the methanol OH donor and the quinazolinone O C acceptor.

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