Man Zhang, Yifan Ru, Shilin Wang, Wen Fu, Tianyu Li, Xusheng Shao, Zhong Li and Wu-Lin Yang
{"title":"Enantioselective synthesis of 2-amino-4H-chromene derivatives with antifungal activities on phytopathogenic fungi†","authors":"Man Zhang, Yifan Ru, Shilin Wang, Wen Fu, Tianyu Li, Xusheng Shao, Zhong Li and Wu-Lin Yang","doi":"10.1039/D4QO00686K","DOIUrl":null,"url":null,"abstract":"<p >An enantioselective cascade allylation/cyclization reaction of 1-(methylthio)-2-nitroenamines with 2-(1-hydroxyallyl)phenols was accomplished by using a chiral Ir(<small>I</small>) catalyst. A broad range of 2-amino-3-nitro-4<em>H</em>-chromene derivatives were obtained in moderate to high yields (55–99%) with moderate to excellent enantioselectivities (50–99% ee). Meanwhile, enantioenriched 2-amino-3-cyano-4<em>H</em>-chromene derivatives could be readily synthesized by using malononitrile in this cascade reaction. The antifungal activities of 2-amino-4<em>H</em>-chromene derivatives were investigated against four species of phytopathogenic fungi and a novel antifungal lead compound with good antifungal activity against <em>Rhizoctonia solani</em> (EC<small><sub>50</sub></small> = 17.43 mg L<small><sup>−1</sup></small>) was found.</p>","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":4.6000,"publicationDate":"2024-05-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Chemistry Frontiers","FirstCategoryId":"92","ListUrlMain":"https://pubs.rsc.org/en/content/articlelanding/2024/qo/d4qo00686k","RegionNum":1,"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
An enantioselective cascade allylation/cyclization reaction of 1-(methylthio)-2-nitroenamines with 2-(1-hydroxyallyl)phenols was accomplished by using a chiral Ir(I) catalyst. A broad range of 2-amino-3-nitro-4H-chromene derivatives were obtained in moderate to high yields (55–99%) with moderate to excellent enantioselectivities (50–99% ee). Meanwhile, enantioenriched 2-amino-3-cyano-4H-chromene derivatives could be readily synthesized by using malononitrile in this cascade reaction. The antifungal activities of 2-amino-4H-chromene derivatives were investigated against four species of phytopathogenic fungi and a novel antifungal lead compound with good antifungal activity against Rhizoctonia solani (EC50 = 17.43 mg L−1) was found.
期刊介绍:
Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.