{"title":"Ruthenium Complexes of Phenylbenzothiazole-Quinoline based Ligands for Selective α-Olefination of Methylazaarenes","authors":"Surabhi Bhatt, Priyal Malpani, Swati Swornaprava Pati, Nitish Kumar, Nattamai Bhuvanesh, Hemant Joshi, Anuj K. Sharma","doi":"10.1002/ejic.202400623","DOIUrl":null,"url":null,"abstract":"<p>This report describes synthesis of a new ligand (<i>E</i>)-<i>N</i>-(4-(benzo[<i>d</i>]thiazol-2-yl)phenyl)-1-(quinolin-2-yl)methanimine (<b>L1</b>) and its three ruthenium(II) arene complexes with [RuCl<sub>2</sub>(<i>p</i>-cymene)]<sub>2</sub> (<b>C1</b>), [RuCl<sub>2</sub>(benzene)]<sub>2</sub> (<b>C2</b>), and [RuCl<sub>2</sub>(hmb)]<sub>2</sub> [hmb=hexamethylbenzene] (<b>C3</b>). The new ligand and complexes were characterized with the help of standard spectroscopic and analytical techniques like <sup>1</sup>H and <sup>13</sup>C{<sup>1</sup>H} Nuclear Magnetic Resonance (NMR), Fourier transform infrared (FTIR), High-resolution mass spectrometry (HRMS), UV-Visible, cyclic voltammetry, and elemental analysis. The structure of ruthenium complex (<b>C1</b>) and its binding mode with ligand were authenticated with the help of single crystal X-ray diffraction. The ruthenium arene complexes (<b>C1-</b>-<b>C3</b>) were used as a catalyst for the α-olefination of Methylazaarenes. First, methylazaarenes were reacted with alcohols under optimized reaction conditions to produce α-olefinated products (up to 66 %) selectively. Among the three ruthenium complexes, <b>C1</b> demonstrated the highest yield of olefinated products with 5 mol % catalyst loading. Finally, selected olefin derivatives were tested for their inhibitory potential towards the aggregation of amyloid-b-40 (A<i>β</i>40) peptide relevant to Alzheimer's disease. Overall, these complexes are promising catalysts for organic transformations, and the synthesized <i>α</i>-olefinated derivatives could have potential applications for the development of therapeutic agents for Alzheimer's disease.</p>","PeriodicalId":38,"journal":{"name":"European Journal of Inorganic Chemistry","volume":"28 2","pages":""},"PeriodicalIF":2.2000,"publicationDate":"2024-10-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"European Journal of Inorganic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/ejic.202400623","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, INORGANIC & NUCLEAR","Score":null,"Total":0}
引用次数: 0
Abstract
This report describes synthesis of a new ligand (E)-N-(4-(benzo[d]thiazol-2-yl)phenyl)-1-(quinolin-2-yl)methanimine (L1) and its three ruthenium(II) arene complexes with [RuCl2(p-cymene)]2 (C1), [RuCl2(benzene)]2 (C2), and [RuCl2(hmb)]2 [hmb=hexamethylbenzene] (C3). The new ligand and complexes were characterized with the help of standard spectroscopic and analytical techniques like 1H and 13C{1H} Nuclear Magnetic Resonance (NMR), Fourier transform infrared (FTIR), High-resolution mass spectrometry (HRMS), UV-Visible, cyclic voltammetry, and elemental analysis. The structure of ruthenium complex (C1) and its binding mode with ligand were authenticated with the help of single crystal X-ray diffraction. The ruthenium arene complexes (C1--C3) were used as a catalyst for the α-olefination of Methylazaarenes. First, methylazaarenes were reacted with alcohols under optimized reaction conditions to produce α-olefinated products (up to 66 %) selectively. Among the three ruthenium complexes, C1 demonstrated the highest yield of olefinated products with 5 mol % catalyst loading. Finally, selected olefin derivatives were tested for their inhibitory potential towards the aggregation of amyloid-b-40 (Aβ40) peptide relevant to Alzheimer's disease. Overall, these complexes are promising catalysts for organic transformations, and the synthesized α-olefinated derivatives could have potential applications for the development of therapeutic agents for Alzheimer's disease.
期刊介绍:
The European Journal of Inorganic Chemistry (2019 ISI Impact Factor: 2.529) publishes Full Papers, Communications, and Minireviews from the entire spectrum of inorganic, organometallic, bioinorganic, and solid-state chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies.
The following journals have been merged to form the two leading journals, European Journal of Inorganic Chemistry and European Journal of Organic Chemistry:
Chemische Berichte
Bulletin des Sociétés Chimiques Belges
Bulletin de la Société Chimique de France
Gazzetta Chimica Italiana
Recueil des Travaux Chimiques des Pays-Bas
Anales de Química
Chimika Chronika
Revista Portuguesa de Química
ACH—Models in Chemistry
Polish Journal of Chemistry
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