Synthesis and Structure Elucidation of Novel Spirooxindole Linked to Ferrocene and Triazole Systems <i>via</i> [3 + 2] Cycloaddition Reaction
In the present work, a novel heterocyclic hybrid of a spirooxindole system was synthesized <i>via</i> the attachment of ferrocene and triazole motifs into an azomethine ylide by [3 + 2] cycloaddition reaction protocol. The X-ray structure of the heterocyclic hybrid (1″<i>R</i>...
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MDPI AG
2022-06-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/13/4095 |
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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 | In the present work, a novel heterocyclic hybrid of a spirooxindole system was synthesized <i>via</i> the attachment of ferrocene and triazole motifs into an azomethine ylide by [3 + 2] cycloaddition reaction protocol. The X-ray structure of the heterocyclic hybrid (1″<i>R</i>,2″<i>S</i>,3<i>R</i>)-2″-(1-(3-chloro-4-fluorophenyl)-5-methyl-1<i>H</i>-1,2,3-triazole-4-carbonyl)-5-methyl-1″-(ferrocin-2-yl)-1″,2″,5″,6″,7″,7a″-hexahydrospiro[indoline-3,3″-pyrrolizin]-2-one revealed very well the expected structure, by using different analytical tools (FTIR and NMR spectroscopy). It crystallized in the triclinic-crystal system and the <i>P</i>-<i>1</i>-space group. The unit cell parameters are <i>a</i> = 9.1442(2) Å, <i>b</i> = 12.0872(3) Å, <i>c</i> = 14.1223(4) Å, <i>α</i> = 102.1700(10)°, <i>β</i> = 97.4190(10)°, <i>γ</i> = 99.1600(10)°, and V = 1484.81(7) Å<sup>3</sup>. There are two molecules per unit cell and one formula unit per asymmetric unit. Hirshfeld analysis was used to study the molecular packing of the heterocyclic hybrid. H···H (50.8%), H···C (14.2%), Cl···H (8.9%), O···H (7.3%), and N···H (5.1%) are the most dominant intermolecular contacts in the crystal structure. O···H, N···H, H···C, F···H, F···C, and O···O are the only contacts that have the characteristic features of short and significant interactions. AIM study indicated predominant covalent characters for the Fe–C interactions. Also, the electron density (ρ(r)) at the bond critical point correlated inversely with the Fe–C distances. |
| first_indexed | 2024-03-09T12:44:31Z |
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| language | English |
| last_indexed | 2024-03-09T12:44:31Z |
| publishDate | 2022-06-01 |
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| spelling | doaj.art-0e6182f3c0744dd0b3d45cd3742b14922023-11-30T22:14:01ZengMDPI AGMolecules1420-30492022-06-012713409510.3390/molecules27134095Synthesis and Structure Elucidation of Novel Spirooxindole Linked to Ferrocene and Triazole Systems <i>via</i> [3 + 2] Cycloaddition ReactionMezna 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, Ibrahimia, 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 ArabiaIn the present work, a novel heterocyclic hybrid of a spirooxindole system was synthesized <i>via</i> the attachment of ferrocene and triazole motifs into an azomethine ylide by [3 + 2] cycloaddition reaction protocol. The X-ray structure of the heterocyclic hybrid (1″<i>R</i>,2″<i>S</i>,3<i>R</i>)-2″-(1-(3-chloro-4-fluorophenyl)-5-methyl-1<i>H</i>-1,2,3-triazole-4-carbonyl)-5-methyl-1″-(ferrocin-2-yl)-1″,2″,5″,6″,7″,7a″-hexahydrospiro[indoline-3,3″-pyrrolizin]-2-one revealed very well the expected structure, by using different analytical tools (FTIR and NMR spectroscopy). It crystallized in the triclinic-crystal system and the <i>P</i>-<i>1</i>-space group. The unit cell parameters are <i>a</i> = 9.1442(2) Å, <i>b</i> = 12.0872(3) Å, <i>c</i> = 14.1223(4) Å, <i>α</i> = 102.1700(10)°, <i>β</i> = 97.4190(10)°, <i>γ</i> = 99.1600(10)°, and V = 1484.81(7) Å<sup>3</sup>. There are two molecules per unit cell and one formula unit per asymmetric unit. Hirshfeld analysis was used to study the molecular packing of the heterocyclic hybrid. H···H (50.8%), H···C (14.2%), Cl···H (8.9%), O···H (7.3%), and N···H (5.1%) are the most dominant intermolecular contacts in the crystal structure. O···H, N···H, H···C, F···H, F···C, and O···O are the only contacts that have the characteristic features of short and significant interactions. AIM study indicated predominant covalent characters for the Fe–C interactions. Also, the electron density (ρ(r)) at the bond critical point correlated inversely with the Fe–C distances.https://www.mdpi.com/1420-3049/27/13/4095spirooxindoleferrocenetriazoleazomethine ylide[3 + 2] cycloaddition (32CA) reaction |
| spellingShingle | Mezna Saleh Altowyan Saied M. Soliman Matti Haukka Nora Hamad Al-Shaalan Aminah A. Alkharboush Assem Barakat Synthesis and Structure Elucidation of Novel Spirooxindole Linked to Ferrocene and Triazole Systems <i>via</i> [3 + 2] Cycloaddition Reaction Molecules spirooxindole ferrocene triazole azomethine ylide [3 + 2] cycloaddition (32CA) reaction |
| title | Synthesis and Structure Elucidation of Novel Spirooxindole Linked to Ferrocene and Triazole Systems <i>via</i> [3 + 2] Cycloaddition Reaction |
| title_full | Synthesis and Structure Elucidation of Novel Spirooxindole Linked to Ferrocene and Triazole Systems <i>via</i> [3 + 2] Cycloaddition Reaction |
| title_fullStr | Synthesis and Structure Elucidation of Novel Spirooxindole Linked to Ferrocene and Triazole Systems <i>via</i> [3 + 2] Cycloaddition Reaction |
| title_full_unstemmed | Synthesis and Structure Elucidation of Novel Spirooxindole Linked to Ferrocene and Triazole Systems <i>via</i> [3 + 2] Cycloaddition Reaction |
| title_short | Synthesis and Structure Elucidation of Novel Spirooxindole Linked to Ferrocene and Triazole Systems <i>via</i> [3 + 2] Cycloaddition Reaction |
| title_sort | synthesis and structure elucidation of novel spirooxindole linked to ferrocene and triazole systems i via i 3 2 cycloaddition reaction |
| topic | spirooxindole ferrocene triazole azomethine ylide [3 + 2] cycloaddition (32CA) reaction |
| url | https://www.mdpi.com/1420-3049/27/13/4095 |
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