Cargando…
Synthesis and Structure Elucidation of Novel Spirooxindole Linked to Ferrocene and Triazole Systems via [3 + 2] Cycloaddition Reaction
In the present work, a novel heterocyclic hybrid of a spirooxindole system was synthesized via 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″R,2″S,3R)-2″-(1-(3-chloro-4-fluorophen...
Autores principales: | , , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2022
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9268063/ https://www.ncbi.nlm.nih.gov/pubmed/35807340 http://dx.doi.org/10.3390/molecules27134095 |
_version_ | 1784743888323346432 |
---|---|
author | Altowyan, Mezna Saleh Soliman, Saied M. Haukka, Matti Al-Shaalan, Nora Hamad Alkharboush, Aminah A. Barakat, Assem |
author_facet | Altowyan, Mezna Saleh Soliman, Saied M. Haukka, Matti Al-Shaalan, Nora Hamad Alkharboush, Aminah A. Barakat, Assem |
author_sort | Altowyan, Mezna Saleh |
collection | PubMed |
description | In the present work, a novel heterocyclic hybrid of a spirooxindole system was synthesized via 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″R,2″S,3R)-2″-(1-(3-chloro-4-fluorophenyl)-5-methyl-1H-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 P-1-space group. The unit cell parameters are a = 9.1442(2) Å, b = 12.0872(3) Å, c = 14.1223(4) Å, α = 102.1700(10)°, β = 97.4190(10)°, γ = 99.1600(10)°, and V = 1484.81(7) Å(3). 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. |
format | Online Article Text |
id | pubmed-9268063 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-92680632022-07-09 Synthesis and Structure Elucidation of Novel Spirooxindole Linked to Ferrocene and Triazole Systems via [3 + 2] Cycloaddition Reaction Altowyan, Mezna Saleh Soliman, Saied M. Haukka, Matti Al-Shaalan, Nora Hamad Alkharboush, Aminah A. Barakat, Assem Molecules Article In the present work, a novel heterocyclic hybrid of a spirooxindole system was synthesized via 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″R,2″S,3R)-2″-(1-(3-chloro-4-fluorophenyl)-5-methyl-1H-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 P-1-space group. The unit cell parameters are a = 9.1442(2) Å, b = 12.0872(3) Å, c = 14.1223(4) Å, α = 102.1700(10)°, β = 97.4190(10)°, γ = 99.1600(10)°, and V = 1484.81(7) Å(3). 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. MDPI 2022-06-25 /pmc/articles/PMC9268063/ /pubmed/35807340 http://dx.doi.org/10.3390/molecules27134095 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Altowyan, Mezna Saleh Soliman, Saied M. Haukka, Matti Al-Shaalan, Nora Hamad Alkharboush, Aminah A. Barakat, Assem Synthesis and Structure Elucidation of Novel Spirooxindole Linked to Ferrocene and Triazole Systems via [3 + 2] Cycloaddition Reaction |
title | Synthesis and Structure Elucidation of Novel Spirooxindole Linked to Ferrocene and Triazole Systems via [3 + 2] Cycloaddition Reaction |
title_full | Synthesis and Structure Elucidation of Novel Spirooxindole Linked to Ferrocene and Triazole Systems via [3 + 2] Cycloaddition Reaction |
title_fullStr | Synthesis and Structure Elucidation of Novel Spirooxindole Linked to Ferrocene and Triazole Systems via [3 + 2] Cycloaddition Reaction |
title_full_unstemmed | Synthesis and Structure Elucidation of Novel Spirooxindole Linked to Ferrocene and Triazole Systems via [3 + 2] Cycloaddition Reaction |
title_short | Synthesis and Structure Elucidation of Novel Spirooxindole Linked to Ferrocene and Triazole Systems via [3 + 2] Cycloaddition Reaction |
title_sort | synthesis and structure elucidation of novel spirooxindole linked to ferrocene and triazole systems via [3 + 2] cycloaddition reaction |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9268063/ https://www.ncbi.nlm.nih.gov/pubmed/35807340 http://dx.doi.org/10.3390/molecules27134095 |
work_keys_str_mv | AT altowyanmeznasaleh synthesisandstructureelucidationofnovelspirooxindolelinkedtoferroceneandtriazolesystemsvia32cycloadditionreaction AT solimansaiedm synthesisandstructureelucidationofnovelspirooxindolelinkedtoferroceneandtriazolesystemsvia32cycloadditionreaction AT haukkamatti synthesisandstructureelucidationofnovelspirooxindolelinkedtoferroceneandtriazolesystemsvia32cycloadditionreaction AT alshaalannorahamad synthesisandstructureelucidationofnovelspirooxindolelinkedtoferroceneandtriazolesystemsvia32cycloadditionreaction AT alkharboushaminaha synthesisandstructureelucidationofnovelspirooxindolelinkedtoferroceneandtriazolesystemsvia32cycloadditionreaction AT barakatassem synthesisandstructureelucidationofnovelspirooxindolelinkedtoferroceneandtriazolesystemsvia32cycloadditionreaction |