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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
| Content Provider | MDPI |
|---|---|
| Author | Altowyan, Mezna Saleh Soliman, Saied M. Haukka, Matti Al-Shaalan, Nora H. Alkharboush, Aminah A. Barakat, Assem |
| Copyright Year | 2021 |
| Description | 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 $(MeOH/NEt_{3}$) 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 $(R^{2}$ = 0.93–0.94). |
| Starting Page | 6 |
| e-ISSN | 20734352 |
| DOI | 10.3390/cryst12010006 |
| Journal | Crystals |
| Issue Number | 1 |
| Volume Number | 12 |
| Language | English |
| Publisher | MDPI |
| Publisher Date | 2021-12-21 |
| Access Restriction | Open |
| Subject Keyword | Crystals Pyrrolo[2,1-a]isoquinoline Azomethine Ylide [3 + 2] Cycloaddition (32ca) Reaction Stereoselective Dft Hirshfeld |
| Content Type | Text |
| Resource Type | Article |
