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

Abstract
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).
Main Authors
Format
Articles Research article
Published
2022
Series
Subjects
Publication in research information system
Publisher
MDPI AG
The permanent address of the publication
https://urn.fi/URN:NBN:fi:jyu-202202071405Use this for linking
Review status
Peer reviewed
ISSN
2073-4352
DOI
https://doi.org/10.3390/cryst12010006
Language
English
Published in
Crystals
Citation
  • Altowyan, M. S., Soliman, S. M., Haukka, M., Al-Shaalan, N. H., Alkharboush, A. A., & Barakat, A. (2022). 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. Crystals, 12(1), Article 6. https://doi.org/10.3390/cryst12010006
License
CC BY 4.0Open Access
Additional information about funding
This work was funded by the Deanship of Scientific Research at Princess Nourah bint Abdulrahman University, through the Research Groups Program Grant no. (RGP-1443-0040).
Copyright© 2021 the Authors

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