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[3+2] Cycloaddition Reaction for the Stereoselective Synthesis of a New Spirooxindole Compound Grafted Imidazo[2,1-b]thiazole Scaffold: Crystal Structure and Computational Study
| Content Provider | MDPI |
|---|---|
| Author | Altowyan, Mezna Saleh Soliman, Saied M. Haukka, Matti Al-Shaalan, Nora Hamad Alkharboush, Aminah A. Barakat, Assem |
| Copyright Year | 2021 |
| Description | A new spirooxindole hybrid engrafted imidazo[2,1-b]thiazole core structure was designed and achieved via [3+2] cycloaddition reaction approach. One multi-component reaction between the ethylene derivative based imidazo[2,1-b]thiazole scaffold with 6-Cl-isatin and the secondary amine under heat conditions afforded the desired compound in a stereoselective manner. The relative absolute configuration was assigned based on single-crystal X-ray diffraction analysis. Hirshfeld calculations for 4 revealed the importance of the H…H (36.8%), H…C (22.9%), Cl…H (10.4%) and S…H (6.6%), as well as the O…H (4.7%), N…H (5.3%), Cl…C (1.6%), Cl…O (1.0%) and N…O (0.5%) contacts in the crystal stability. DFT calculations showed excellent straight-line correlations $(R^{2}$ = 0.9776–0.9962) between the calculated and experimental geometric parameters. The compound has polar nature (3.1664 Debye). TD-DFT and GIAO calculations were used to assign and correlate the experimental UV-Vis and NMR spectra, respectively. |
| Starting Page | 5 |
| e-ISSN | 20734352 |
| DOI | 10.3390/cryst12010005 |
| Journal | Crystals |
| Issue Number | 1 |
| Volume Number | 12 |
| Language | English |
| Publisher | MDPI |
| Publisher Date | 2021-12-21 |
| Access Restriction | Open |
| Subject Keyword | Crystals Medicinal Chemistry Spirooxindole Imidazo[2,1-b]thiazole Azomethine Ylide [3+2] Cycloaddition (32ca) Reaction |
| Content Type | Text |
| Resource Type | Article |
