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Chitosan–Cu Catalyzed Novel Ferrocenated Spiropyrrolidines: Green Synthesis, Single Crystal X-ray Diffraction, Hirshfeld Surface and Antibacterial Studies

Chitosan-bounded copper (chitosan–Cu) was introduced for green synthesis of novel ferrocenated spiropyrrolidine hybrids, namely 3′-(4-.bromobenzoyl)-5′-(4-hydroxybenzyl)-4′-ferrocenylspiro[indoline-3,2′-pyrrolidin]-2-one and 3′-(4-bromobenzoyl)-4′-ferrocenylspiro[indoline-3,2′-pyrrolidin]-2-one, in...

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Autores principales: Asad, Mohammad, Arshad, Muhammad Nadeem, Asiri, Abdullah M., Rahman, Mohammed M., Kumaran, Snigdha, Thorakkattil Neerankuzhiyil, Mohammed Musthafa
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9867216/
https://www.ncbi.nlm.nih.gov/pubmed/36679308
http://dx.doi.org/10.3390/polym15020429
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author Asad, Mohammad
Arshad, Muhammad Nadeem
Asiri, Abdullah M.
Rahman, Mohammed M.
Kumaran, Snigdha
Thorakkattil Neerankuzhiyil, Mohammed Musthafa
author_facet Asad, Mohammad
Arshad, Muhammad Nadeem
Asiri, Abdullah M.
Rahman, Mohammed M.
Kumaran, Snigdha
Thorakkattil Neerankuzhiyil, Mohammed Musthafa
author_sort Asad, Mohammad
collection PubMed
description Chitosan-bounded copper (chitosan–Cu) was introduced for green synthesis of novel ferrocenated spiropyrrolidine hybrids, namely 3′-(4-.bromobenzoyl)-5′-(4-hydroxybenzyl)-4′-ferrocenylspiro[indoline-3,2′-pyrrolidin]-2-one and 3′-(4-bromobenzoyl)-4′-ferrocenylspiro[indoline-3,2′-pyrrolidin]-2-one, in good yield. A one-pot three-component 1,3-dipolar cycloaddition reaction was employed for the formation of spiropyrrolidines from 1-(4-bromophenyl)-ferrocene-prop-2-en-1-one and azomethine ylides, which were developed in situ from tyrosine, glycine, and isatin, respectively. Various spectroscopic methods were used to establish the structures of spiropyrrolidines, and a single crystal X-ray diffraction study of a spiropyrrolidine provided additional confirmation. The crystallographic study revealed that compound 3a has one independent molecule in its unit cell, which is correlated with Hirshfeld surface analysis, and describes intramolecular contacts adversely. The highly yielded products in green conditions were determined for their antibacterial significance and were found to have good activity against Gram-positive and Gram-negative bacterial strains.
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spelling pubmed-98672162023-01-22 Chitosan–Cu Catalyzed Novel Ferrocenated Spiropyrrolidines: Green Synthesis, Single Crystal X-ray Diffraction, Hirshfeld Surface and Antibacterial Studies Asad, Mohammad Arshad, Muhammad Nadeem Asiri, Abdullah M. Rahman, Mohammed M. Kumaran, Snigdha Thorakkattil Neerankuzhiyil, Mohammed Musthafa Polymers (Basel) Article Chitosan-bounded copper (chitosan–Cu) was introduced for green synthesis of novel ferrocenated spiropyrrolidine hybrids, namely 3′-(4-.bromobenzoyl)-5′-(4-hydroxybenzyl)-4′-ferrocenylspiro[indoline-3,2′-pyrrolidin]-2-one and 3′-(4-bromobenzoyl)-4′-ferrocenylspiro[indoline-3,2′-pyrrolidin]-2-one, in good yield. A one-pot three-component 1,3-dipolar cycloaddition reaction was employed for the formation of spiropyrrolidines from 1-(4-bromophenyl)-ferrocene-prop-2-en-1-one and azomethine ylides, which were developed in situ from tyrosine, glycine, and isatin, respectively. Various spectroscopic methods were used to establish the structures of spiropyrrolidines, and a single crystal X-ray diffraction study of a spiropyrrolidine provided additional confirmation. The crystallographic study revealed that compound 3a has one independent molecule in its unit cell, which is correlated with Hirshfeld surface analysis, and describes intramolecular contacts adversely. The highly yielded products in green conditions were determined for their antibacterial significance and were found to have good activity against Gram-positive and Gram-negative bacterial strains. MDPI 2023-01-13 /pmc/articles/PMC9867216/ /pubmed/36679308 http://dx.doi.org/10.3390/polym15020429 Text en © 2023 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
Asad, Mohammad
Arshad, Muhammad Nadeem
Asiri, Abdullah M.
Rahman, Mohammed M.
Kumaran, Snigdha
Thorakkattil Neerankuzhiyil, Mohammed Musthafa
Chitosan–Cu Catalyzed Novel Ferrocenated Spiropyrrolidines: Green Synthesis, Single Crystal X-ray Diffraction, Hirshfeld Surface and Antibacterial Studies
title Chitosan–Cu Catalyzed Novel Ferrocenated Spiropyrrolidines: Green Synthesis, Single Crystal X-ray Diffraction, Hirshfeld Surface and Antibacterial Studies
title_full Chitosan–Cu Catalyzed Novel Ferrocenated Spiropyrrolidines: Green Synthesis, Single Crystal X-ray Diffraction, Hirshfeld Surface and Antibacterial Studies
title_fullStr Chitosan–Cu Catalyzed Novel Ferrocenated Spiropyrrolidines: Green Synthesis, Single Crystal X-ray Diffraction, Hirshfeld Surface and Antibacterial Studies
title_full_unstemmed Chitosan–Cu Catalyzed Novel Ferrocenated Spiropyrrolidines: Green Synthesis, Single Crystal X-ray Diffraction, Hirshfeld Surface and Antibacterial Studies
title_short Chitosan–Cu Catalyzed Novel Ferrocenated Spiropyrrolidines: Green Synthesis, Single Crystal X-ray Diffraction, Hirshfeld Surface and Antibacterial Studies
title_sort chitosan–cu catalyzed novel ferrocenated spiropyrrolidines: green synthesis, single crystal x-ray diffraction, hirshfeld surface and antibacterial studies
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9867216/
https://www.ncbi.nlm.nih.gov/pubmed/36679308
http://dx.doi.org/10.3390/polym15020429
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