A1 Journal article (refereed)
[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 (2022)

Altowyan, M. S., Soliman, S. M., Haukka, M., Al-Shaalan, N. H., Alkharboush, A. A., & Barakat, A. (2022). [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. Crystals, 12(1), Article 5. https://doi.org/10.3390/cryst12010005

JYU authors or editors

Publication details

All authors or editors: Altowyan, Mezna Saleh; Soliman, Saied M.; Haukka, Matti; Al-Shaalan, Nora Hamad; Alkharboush, Aminah A.; Barakat, Assem

Journal or series: Crystals

eISSN: 2073-4352

Publication year: 2022

Volume: 12

Issue number: 1

Article number: 5

Publisher: MDPI

Publication country: Switzerland

Publication language: English

DOI: https://doi.org/10.3390/cryst12010005

Publication open access: Openly available

Publication channel open access: Open Access channel

Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/79573

Abstract

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.

Keywords: heterocyclic compounds; crystals

Free keywords: spirooxindole; imidazo[2,1-b]thiazole; azomethine ylide; [3+2] cycloaddition (32CA) reaction

Contributing organizations

Ministry reporting: Yes

Reporting Year: 2022

JUFO rating: 1