[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

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 condi...

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Bibliographic Details
Published in:Crystals (Basel) 2022-01, Vol.12 (1), p.5
Main Authors: Altowyan, Mezna, Soliman, Saied, Haukka, Matti, Al-Shaalan, Nora, Alkharboush, Aminah, Barakat, Assem
Format: Article
Language:English
Subjects:
[3+2] cycloaddition (32CA) reaction
Alzheimer's disease
azomethine ylide
Cancer therapies
Chemical synthesis
Crystal structure
Cycloaddition
Drug resistance
imidazo[2,1-b]thiazole
Mathematical analysis
Medical research
NMR
Nuclear magnetic resonance
Proteins
Scaffolds
Single crystals
spirooxindole
Stereoselectivity
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Summary: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 (R2 = 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.
ISSN:2073-4352
2073-4352
DOI:10.3390/cryst12010005