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RESEARCH PRODUCT
Synthesis of Unexpected Dimethyl 2-(4-Chlorophenyl)-2,3-dihydropyrrolo[2,1-a]isoquinoline-1,3-dicarboxylate via Hydrolysis/Cycloaddition/Elimination Cascades: Single Crystal X-ray and Chemical Structure Insights
Mezna AltowyanSaied SolimanMatti HaukkaNora Al-shaalanAminah AlkharboushAssem Barakatsubject
kemiallinen synteesiCrystallographystereoselectivepyrrolo[21-a]isoquinolineGeneral Chemical Engineeringtiheysfunktionaaliteoria[3 + 2] cycloaddition (32CA) reactionpyrrolo[21-<i>a</i>]isoquinolineCondensed Matter PhysicsDFTHirshfeldpyrrolo[21-<i>a</i>]isoquinoline; azomethine ylide; [3 + 2] cycloaddition (32CA) reaction; stereoselective; DFT; HirshfeldInorganic Chemistryazomethine ylideQD901-999General Materials Sciencetyppiyhdisteetheterosykliset yhdisteetröntgenkristallografiadescription
Hydrolysis/[3 + 2] cycloaddition/elimination cascades employed for the synthesis of unexpected tricyclic compound derived from isoquinoline. Reaction of ethylene derivative 1 with the isoquinoline ester iminium ion 2 in alkaline medium (MeOH/NEt3) under reflux for 1 h resulted in the formation of the fused pyrrolo[2,1-a]isoquinoline derivative 3. Its structure was elucidated by X-ray single crystal and other spectrophotometric tools. Hirshfeld calculations for 3 and its crystal structure analysis revealed the importance of the short O…H (19.1%) contacts and the relatively long H…C (17.1%), Cl…H (10.6%) and C…C (6.1%) interactions in the molecular packing. DFT calculations were used to compute the electronic and spectroscopic properties of the studied system. The studied compound has polar nature (3.5953 Debye). TD-DFT calculations assigned the shortest wavelength band (220 nm) to the HOMO−1→LUMO+2 (57%), HOMO−1→LUMO+4 (14%) mixed excitations. The calculated NMR chemical shifts correlated very well with the experimental data (R2 = 0.93–0.94).
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2021-12-21 | Crystals; Volume 12; Issue 1; Pages: 6 |