dc.contributor.author | Barakat, Assem | |
dc.contributor.author | Haukka, Matti | |
dc.contributor.author | Soliman, Saied M. | |
dc.contributor.author | Ali, M. | |
dc.contributor.author | Al-Majid, Abdullah Mohammed | |
dc.contributor.author | El-Faham, Ayman | |
dc.contributor.author | Domingo, Luis R. | |
dc.date.accessioned | 2022-01-05T09:55:40Z | |
dc.date.available | 2022-01-05T09:55:40Z | |
dc.date.issued | 2021 | |
dc.identifier.citation | Barakat, A., Haukka, M., Soliman, S. M., Ali, M., Al-Majid, A. M., El-Faham, A., & Domingo, L. R. (2021). Straightforward Regio- and Diastereoselective Synthesis, Molecular Structure, Intermolecular Interactions and Mechanistic Study of Spirooxindole-Engrafted Rhodanine Analogs. <i>Molecules</i>, <i>26</i>(23), Article 7276. <a href="https://doi.org/10.3390/molecules26237276" target="_blank">https://doi.org/10.3390/molecules26237276</a> | |
dc.identifier.other | CONVID_103619248 | |
dc.identifier.uri | https://jyx.jyu.fi/handle/123456789/79238 | |
dc.description.abstract | Straightforward regio- and diastereoselective synthesis of bi-spirooxindole-engrafted rhodanine analogs 5a–d were achieved by one-pot multicomponent [3 + 2] cycloaddition (32CA) reaction of stabilized azomethine ylide (AYs 3a–d) generated in situ by condensation of L-thioproline and 6-chloro-isatin with (E)-2-(5-(4-chlorobenzylidene)-2,4-dioxothiazolidin-3-yl)-N-(2-morpholinoethyl)acetamide. The bi-spirooxindole-engrafted rhodanine analogs were constructed with excellent diastereo- and regioselectivity along with high chemical yield. X-ray crystallographic investigations for hybrid 5a revealed the presence of four contiguous stereocenters related to C11, C12, C19 and C22 of the spiro structure. Hirshfeld calculations indicated the presence of many short intermolecular contacts such as Cl...C, S...S, S...H, O...H, N...H, H...C, C...C and H...H interactions. These contacts played a very important role in the crystal stability. The polar nature of the 32CA reaction was studied by analysis of the conceptual DFT reactivity indices. Theoretical study of this 32CA reaction indicated that it takes place through a non-concerted two-stage one-step mechanism associated with the nucleophilic attack of AY 3a to the electrophilic ethylene derivative | en |
dc.format.mimetype | application/pdf | |
dc.language.iso | eng | |
dc.publisher | MDPI AG | |
dc.relation.ispartofseries | Molecules | |
dc.rights | CC BY 4.0 | |
dc.subject.other | spirooxindole | |
dc.subject.other | rhodanine | |
dc.subject.other | azomethine ylides | |
dc.subject.other | [3 + 2] cycloaddition (32CA) reactions | |
dc.subject.other | hydrogen bonding | |
dc.subject.other | Hirshfeld DFT | |
dc.subject.other | supernucleophiles | |
dc.title | Straightforward Regio- and Diastereoselective Synthesis, Molecular Structure, Intermolecular Interactions and Mechanistic Study of Spirooxindole-Engrafted Rhodanine Analogs | |
dc.type | article | |
dc.identifier.urn | URN:NBN:fi:jyu-202201051017 | |
dc.contributor.laitos | Kemian laitos | fi |
dc.contributor.laitos | Department of Chemistry | en |
dc.contributor.oppiaine | Epäorgaaninen ja analyyttinen kemia | fi |
dc.contributor.oppiaine | Epäorgaaninen kemia | fi |
dc.contributor.oppiaine | Inorganic and Analytical Chemistry | en |
dc.contributor.oppiaine | Inorganic Chemistry | en |
dc.type.uri | http://purl.org/eprint/type/JournalArticle | |
dc.type.coar | http://purl.org/coar/resource_type/c_2df8fbb1 | |
dc.description.reviewstatus | peerReviewed | |
dc.relation.issn | 1420-3049 | |
dc.relation.numberinseries | 23 | |
dc.relation.volume | 26 | |
dc.type.version | publishedVersion | |
dc.rights.copyright | © 2021 by the authors. Licensee MDPI, Basel, Switzerland. | |
dc.rights.accesslevel | openAccess | fi |
dc.subject.yso | tiheysfunktionaaliteoria | |
dc.subject.yso | vetysidokset | |
dc.subject.yso | heterosykliset yhdisteet | |
dc.format.content | fulltext | |
jyx.subject.uri | http://www.yso.fi/onto/yso/p28852 | |
jyx.subject.uri | http://www.yso.fi/onto/yso/p38131 | |
jyx.subject.uri | http://www.yso.fi/onto/yso/p38837 | |
dc.rights.url | https://creativecommons.org/licenses/by/4.0/ | |
dc.relation.doi | 10.3390/molecules26237276 | |
jyx.fundinginformation | The authors would like to extend their sincere appreciation to the Researchers Supporting Project (RSP-2021/64), King Saud University, Riyadh, Saudi Arabia, and the Ministerio de Ciencias, Innovación y Universidades of the Spanish Government, project PID2019-110776GB-I00 (AEI/FEDER, UE). | |
dc.type.okm | A1 | |