dc.contributor.author | Altowyan, Mezna Saleh | |
dc.contributor.author | Soliman, Saied M. | |
dc.contributor.author | Haukka, Matti | |
dc.contributor.author | Al-Shaalan, Nora H. | |
dc.contributor.author | Alkharboush, Aminah A. | |
dc.contributor.author | Barakat, Assem | |
dc.date.accessioned | 2022-02-07T06:58:06Z | |
dc.date.available | 2022-02-07T06:58:06Z | |
dc.date.issued | 2022 | |
dc.identifier.citation | Altowyan, M. S., Soliman, S. M., Haukka, M., Al-Shaalan, N. H., Alkharboush, A. A., & Barakat, A. (2022). Synthesis of Unexpected Dimethyl 2-(4-Chlorophenyl)-2,3-dihydropyrrolo[2,1-a]isoquinoline-1,3-dicarboxylate via Hydrolysis/Cycloaddition/Elimination Cascades : Single Crystal X-ray and Chemical Structure Insights. <i>Crystals</i>, <i>12</i>(1), Article 6. <a href="https://doi.org/10.3390/cryst12010006" target="_blank">https://doi.org/10.3390/cryst12010006</a> | |
dc.identifier.other | CONVID_104135575 | |
dc.identifier.uri | https://jyx.jyu.fi/handle/123456789/79647 | |
dc.description.abstract | Hydrolysis/[3 + 2] cycloaddition/elimination cascades employed for the synthesis of unexpected tricyclic compound derived from isoquinoline. Reaction of ethylene derivative 1 with the isoquinoline ester iminium ion 2 in alkaline medium (MeOH/NEt3) under reflux for 1 h resulted in the formation of the fused pyrrolo[2,1-a]isoquinoline derivative 3. Its structure was elucidated by X-ray single crystal and other spectrophotometric tools. Hirshfeld calculations for 3 and its crystal structure analysis revealed the importance of the short O…H (19.1%) contacts and the relatively long H…C (17.1%), Cl…H (10.6%) and C…C (6.1%) interactions in the molecular packing. DFT calculations were used to compute the electronic and spectroscopic properties of the studied system. The studied compound has polar nature (3.5953 Debye). TD-DFT calculations assigned the shortest wavelength band (220 nm) to the HOMO−1→LUMO+2 (57%), HOMO−1→LUMO+4 (14%) mixed excitations. The calculated NMR chemical shifts correlated very well with the experimental data (R2 = 0.93–0.94). | en |
dc.format.mimetype | application/pdf | |
dc.language.iso | eng | |
dc.publisher | MDPI AG | |
dc.relation.ispartofseries | Crystals | |
dc.rights | CC BY 4.0 | |
dc.subject.other | pyrrolo[2,1-a]isoquinoline | |
dc.subject.other | azomethine ylide | |
dc.subject.other | [3 + 2] cycloaddition (32CA) reaction | |
dc.subject.other | stereoselective | |
dc.subject.other | DFT | |
dc.subject.other | Hirshfeld | |
dc.title | Synthesis of Unexpected Dimethyl 2-(4-Chlorophenyl)-2,3-dihydropyrrolo[2,1-a]isoquinoline-1,3-dicarboxylate via Hydrolysis/Cycloaddition/Elimination Cascades : Single Crystal X-ray and Chemical Structure Insights | |
dc.type | research article | |
dc.identifier.urn | URN:NBN:fi:jyu-202202071405 | |
dc.contributor.laitos | Kemian laitos | fi |
dc.contributor.laitos | Department of Chemistry | en |
dc.contributor.oppiaine | Epäorgaaninen kemia | fi |
dc.contributor.oppiaine | Epäorgaaninen ja analyyttinen kemia | fi |
dc.contributor.oppiaine | Inorganic Chemistry | en |
dc.contributor.oppiaine | Inorganic and Analytical 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 | 2073-4352 | |
dc.relation.numberinseries | 1 | |
dc.relation.volume | 12 | |
dc.type.version | publishedVersion | |
dc.rights.copyright | © 2021 the Authors | |
dc.rights.accesslevel | openAccess | fi |
dc.type.publication | article | |
dc.subject.yso | typpiyhdisteet | |
dc.subject.yso | röntgenkristallografia | |
dc.subject.yso | tiheysfunktionaaliteoria | |
dc.subject.yso | kemiallinen synteesi | |
dc.subject.yso | heterosykliset yhdisteet | |
dc.format.content | fulltext | |
jyx.subject.uri | http://www.yso.fi/onto/yso/p640 | |
jyx.subject.uri | http://www.yso.fi/onto/yso/p29058 | |
jyx.subject.uri | http://www.yso.fi/onto/yso/p28852 | |
jyx.subject.uri | http://www.yso.fi/onto/yso/p8468 | |
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/cryst12010006 | |
jyx.fundinginformation | This work was funded by the Deanship of Scientific Research at Princess Nourah bint Abdulrahman University, through the Research Groups Program Grant no. (RGP-1443-0040). | |
dc.type.okm | A1 | |