Pari Keerthana , Sundararajan Suresh , Fazlur Rahman Nawaz Khan
{"title":"Facile synthesis of functionalized quinolinones in a green reaction medium and their photophysical properties†","authors":"Pari Keerthana , Sundararajan Suresh , Fazlur Rahman Nawaz Khan","doi":"10.1039/d4ob01390e","DOIUrl":null,"url":null,"abstract":"<div><div>A facile and green chemical approach was successfully developed to construct functionalized quinolinones utilizing substituted alcohols, alkyl acetoacetate, and α-bromo ketones. Various quinolinones bearing either electron-rich or electron-deficient groups at different positions were synthesized in moderate to good yields under mild reaction conditions. The plausible mechanistic pathway for this transformation is supported by experimental evidence and control experiments. This simple approach for synthesizing quinolinones could open new avenues for discovering novel biological and pharmaceutical compounds. The use of affordable nickel catalysts, mild reaction conditions, operational simplicity, and high atom economy are attractive features of this method. Furthermore, the synthetic efficiency has been demonstrated through gram-scale experiments. Our research also provides valuable insights into the photophysical properties of the synthesized derivatives. Notably, compound exhibited the highest Stokes shift (216 nm) in DCM solvent. Furthermore, compounds and showed positive solvatochromism, displaying a stronger emission as the solvent polarity increased. Additionally, compound displayed aggregation-induced emission (AIE) properties in a DMSO : water mixture, making it suitable for use as a security ink, highlighting its potential applications in various fields.</div></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"23 1","pages":"Pages 126-137"},"PeriodicalIF":2.9000,"publicationDate":"2024-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1477052024009868","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
A facile and green chemical approach was successfully developed to construct functionalized quinolinones utilizing substituted alcohols, alkyl acetoacetate, and α-bromo ketones. Various quinolinones bearing either electron-rich or electron-deficient groups at different positions were synthesized in moderate to good yields under mild reaction conditions. The plausible mechanistic pathway for this transformation is supported by experimental evidence and control experiments. This simple approach for synthesizing quinolinones could open new avenues for discovering novel biological and pharmaceutical compounds. The use of affordable nickel catalysts, mild reaction conditions, operational simplicity, and high atom economy are attractive features of this method. Furthermore, the synthetic efficiency has been demonstrated through gram-scale experiments. Our research also provides valuable insights into the photophysical properties of the synthesized derivatives. Notably, compound exhibited the highest Stokes shift (216 nm) in DCM solvent. Furthermore, compounds and showed positive solvatochromism, displaying a stronger emission as the solvent polarity increased. Additionally, compound displayed aggregation-induced emission (AIE) properties in a DMSO : water mixture, making it suitable for use as a security ink, highlighting its potential applications in various fields.
期刊介绍:
Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.