[3+2] Cycloaddition Reaction for the Stereoselective Synthesis of a New Spirooxindole Compound Grafted Imidazo[2,1-<em>b</em>]thiazole Scaffold: Crystal Structure and Computational Study
A new spirooxindole hybrid engrafted imidazo[2,1-<i>b</i>]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-<i>b</i>]thiazole scaffold with 6-Cl-isatin an...
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| Format: | Article |
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MDPI AG
2021-12-01
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| Series: | Crystals |
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| Online Access: | https://www.mdpi.com/2073-4352/12/1/5 |
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| author | Mezna Saleh Altowyan Saied M. Soliman Matti Haukka Nora Hamad Al-Shaalan Aminah A. Alkharboush Assem Barakat |
| author_facet | Mezna Saleh Altowyan Saied M. Soliman Matti Haukka Nora Hamad Al-Shaalan Aminah A. Alkharboush Assem Barakat |
| author_sort | Mezna Saleh Altowyan |
| collection | DOAJ |
| description | A new spirooxindole hybrid engrafted imidazo[2,1-<i>b</i>]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-<i>b</i>]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 <b>4</b> 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<sup>2</sup> = 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. |
| first_indexed | 2024-03-10T01:41:11Z |
| format | Article |
| id | doaj.art-3ddd9d6b58784888ba0479df02717398 |
| institution | Directory Open Access Journal |
| issn | 2073-4352 |
| language | English |
| last_indexed | 2024-03-10T01:41:11Z |
| publishDate | 2021-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Crystals |
| spelling | doaj.art-3ddd9d6b58784888ba0479df027173982023-11-23T13:23:43ZengMDPI AGCrystals2073-43522021-12-01121510.3390/cryst12010005[3+2] Cycloaddition Reaction for the Stereoselective Synthesis of a New Spirooxindole Compound Grafted Imidazo[2,1-<em>b</em>]thiazole Scaffold: Crystal Structure and Computational StudyMezna Saleh Altowyan0Saied M. Soliman1Matti Haukka2Nora Hamad Al-Shaalan3Aminah A. Alkharboush4Assem Barakat5Department of Chemistry, College of Science, Princess Nourah bint Abdulrahman University, P.O. Box 84428, Riyadh 11671, Saudi ArabiaDepartment of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Alexandria 21321, EgyptDepartment of Chemistry, University of Jyväskylä, P.O. Box 35, FI-40014 Jyväskylä, FinlandDepartment of Chemistry, College of Science, Princess Nourah bint Abdulrahman University, P.O. Box 84428, Riyadh 11671, Saudi ArabiaDepartment of Chemistry, College of Science, Princess Nourah bint Abdulrahman University, P.O. Box 84428, Riyadh 11671, Saudi ArabiaDepartment of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaA new spirooxindole hybrid engrafted imidazo[2,1-<i>b</i>]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-<i>b</i>]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 <b>4</b> 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<sup>2</sup> = 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.https://www.mdpi.com/2073-4352/12/1/5spirooxindoleimidazo[2,1-<i>b</i>]thiazoleazomethine ylide[3+2] cycloaddition (32CA) reaction |
| spellingShingle | Mezna Saleh Altowyan Saied M. Soliman Matti Haukka Nora Hamad Al-Shaalan Aminah A. Alkharboush Assem Barakat [3+2] Cycloaddition Reaction for the Stereoselective Synthesis of a New Spirooxindole Compound Grafted Imidazo[2,1-<em>b</em>]thiazole Scaffold: Crystal Structure and Computational Study Crystals spirooxindole imidazo[2,1-<i>b</i>]thiazole azomethine ylide [3+2] cycloaddition (32CA) reaction |
| title | [3+2] Cycloaddition Reaction for the Stereoselective Synthesis of a New Spirooxindole Compound Grafted Imidazo[2,1-<em>b</em>]thiazole Scaffold: Crystal Structure and Computational Study |
| title_full | [3+2] Cycloaddition Reaction for the Stereoselective Synthesis of a New Spirooxindole Compound Grafted Imidazo[2,1-<em>b</em>]thiazole Scaffold: Crystal Structure and Computational Study |
| title_fullStr | [3+2] Cycloaddition Reaction for the Stereoselective Synthesis of a New Spirooxindole Compound Grafted Imidazo[2,1-<em>b</em>]thiazole Scaffold: Crystal Structure and Computational Study |
| title_full_unstemmed | [3+2] Cycloaddition Reaction for the Stereoselective Synthesis of a New Spirooxindole Compound Grafted Imidazo[2,1-<em>b</em>]thiazole Scaffold: Crystal Structure and Computational Study |
| title_short | [3+2] Cycloaddition Reaction for the Stereoselective Synthesis of a New Spirooxindole Compound Grafted Imidazo[2,1-<em>b</em>]thiazole Scaffold: Crystal Structure and Computational Study |
| title_sort | 3 2 cycloaddition reaction for the stereoselective synthesis of a new spirooxindole compound grafted imidazo 2 1 em b em thiazole scaffold crystal structure and computational study |
| topic | spirooxindole imidazo[2,1-<i>b</i>]thiazole azomethine ylide [3+2] cycloaddition (32CA) reaction |
| url | https://www.mdpi.com/2073-4352/12/1/5 |
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