{"title":"以过期硫酸链霉素为原料,超声化学合成铜螯合物,作为水环境中绿色合成1,4-二取代三唑的可持续催化剂","authors":"Neetu Mev , Yachana Jain , Lalita Yadav , Priya Sharma , Madhu Agarwal , Ragini Gupta","doi":"10.1016/j.tet.2025.134564","DOIUrl":null,"url":null,"abstract":"<div><div>This research work introduces a pioneering strategy for harnessing the potential of expired streptomycin sulfate as its copper chelate to catalyze the synthesis of biologically important 1,4-disubstituted-1,2,3-triazoles efficiently. The efficacy of this catalyst is showcased by the sonochemical 1,3-dipolar cycloaddition process, yielding 1,4-disubstituted-1,2,3-triazoles at 40 °C using a promotor ligand <span>l</span>-phenylalanine within 30 min in >90 % yield in aqueous media with high purity. The biocompatible promoter ligand assists the STR Cu chelate to enhance the reaction rate by stabilizing the Cu(I) oxidation state and preventing its undesirable disproportionation, thus increasing the yield of the intended product. The synthesized catalyst demonstrates extensive substrate compatibility and works equally well with precursors containing both electron donating and withdrawing groups (<strong>4–25</strong>). Additionally, all the synthesized compounds, as well as the catalyst, have been duly characterized by the usual analytical and spectroscopic techniques. Furthermore, the catalyst could be reused up to four cycles without a significant reduction in its catalytic performance.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"177 ","pages":"Article 134564"},"PeriodicalIF":2.1000,"publicationDate":"2025-02-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Sonochemically synthesized copper chelate from expired streptomycin sulfate as a sustainable catalyst for green synthesis of 1,4-disubstituted triazoles in aqueous medium\",\"authors\":\"Neetu Mev , Yachana Jain , Lalita Yadav , Priya Sharma , Madhu Agarwal , Ragini Gupta\",\"doi\":\"10.1016/j.tet.2025.134564\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>This research work introduces a pioneering strategy for harnessing the potential of expired streptomycin sulfate as its copper chelate to catalyze the synthesis of biologically important 1,4-disubstituted-1,2,3-triazoles efficiently. The efficacy of this catalyst is showcased by the sonochemical 1,3-dipolar cycloaddition process, yielding 1,4-disubstituted-1,2,3-triazoles at 40 °C using a promotor ligand <span>l</span>-phenylalanine within 30 min in >90 % yield in aqueous media with high purity. The biocompatible promoter ligand assists the STR Cu chelate to enhance the reaction rate by stabilizing the Cu(I) oxidation state and preventing its undesirable disproportionation, thus increasing the yield of the intended product. The synthesized catalyst demonstrates extensive substrate compatibility and works equally well with precursors containing both electron donating and withdrawing groups (<strong>4–25</strong>). Additionally, all the synthesized compounds, as well as the catalyst, have been duly characterized by the usual analytical and spectroscopic techniques. Furthermore, the catalyst could be reused up to four cycles without a significant reduction in its catalytic performance.</div></div>\",\"PeriodicalId\":437,\"journal\":{\"name\":\"Tetrahedron\",\"volume\":\"177 \",\"pages\":\"Article 134564\"},\"PeriodicalIF\":2.1000,\"publicationDate\":\"2025-02-28\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Tetrahedron\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0040402025001206\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040402025001206","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
摘要
这项研究工作介绍了一种开创性的策略,利用过期硫酸链霉素作为其铜螯合物的潜力,高效催化合成具有重要生物意义的 1,4-二取代-1,2,3-三唑。这种催化剂的功效体现在声化学 1,3 双极环加成过程中,使用促进配体苯丙氨酸,在水介质中于 40 °C 下 30 分钟内生成 1,4-二取代-1,2,3-三唑,收率达 90%,纯度高。生物相容性促进配体通过稳定 Cu(I)的氧化态并防止其发生不应有的歧化反应,协助 STR Cu 螯合物提高反应速率,从而提高了预期产物的产率。合成的催化剂具有广泛的底物兼容性,对含有电子供体和电子汲取基团(4-25)的前体同样有效。此外,所有合成的化合物和催化剂都已通过常用的分析和光谱技术进行了适当的表征。此外,催化剂可重复使用四次,而其催化性能不会明显降低。
Sonochemically synthesized copper chelate from expired streptomycin sulfate as a sustainable catalyst for green synthesis of 1,4-disubstituted triazoles in aqueous medium
This research work introduces a pioneering strategy for harnessing the potential of expired streptomycin sulfate as its copper chelate to catalyze the synthesis of biologically important 1,4-disubstituted-1,2,3-triazoles efficiently. The efficacy of this catalyst is showcased by the sonochemical 1,3-dipolar cycloaddition process, yielding 1,4-disubstituted-1,2,3-triazoles at 40 °C using a promotor ligand l-phenylalanine within 30 min in >90 % yield in aqueous media with high purity. The biocompatible promoter ligand assists the STR Cu chelate to enhance the reaction rate by stabilizing the Cu(I) oxidation state and preventing its undesirable disproportionation, thus increasing the yield of the intended product. The synthesized catalyst demonstrates extensive substrate compatibility and works equally well with precursors containing both electron donating and withdrawing groups (4–25). Additionally, all the synthesized compounds, as well as the catalyst, have been duly characterized by the usual analytical and spectroscopic techniques. Furthermore, the catalyst could be reused up to four cycles without a significant reduction in its catalytic performance.
期刊介绍:
Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry.
Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters.
Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.