Ying Lv, Li Chen, Xinghan Yun, Kun Li, Shengjiao Yan
{"title":"Cascade reaction of 3-formylchromones: Highly selective synthesis of 4-oxo-3-(1H-pyrrol-3-yl)-4H-chromenes","authors":"Ying Lv, Li Chen, Xinghan Yun, Kun Li, Shengjiao Yan","doi":"10.1016/j.gresc.2022.10.003","DOIUrl":null,"url":null,"abstract":"<div><p>A novel method for the preparation of highly functionalized 4-oxo-3-(1<em>H</em>-pyrrol-3-yl)-4<em>H</em>-chromenes (OPCMs) from 3-formylchromones and <em>α</em>-isocyanoacetates <em>via</em> an unprecedented three-component [1 + 1 + 3] cycloaddition reaction in one pot was developed. The three-component cascade reaction was enabled by refluxing a mixture of the substrates in 1,4-dioxane in the presence of Ag<sub>2</sub>CO<sub>3</sub> as a Lewis acid promoter. As a result, a series of functionalized pyrroles (OPCMs, <strong>3</strong>), was prepared regioselectively and in high yields (80%–88%) through the formation of three bonds. This protocol can be used in the synthesis of OPCMs rather than through conventional, multi-step reactions and is suitable for both combinatorial and parallel syntheses of pyrroles.</p></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 2","pages":"Pages 94-101"},"PeriodicalIF":0.0000,"publicationDate":"2024-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666554922001028/pdfft?md5=10d8602b21bda7cbfadf0c6ef0c7a753&pid=1-s2.0-S2666554922001028-main.pdf","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Green Synthesis and Catalysis","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S2666554922001028","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0
Abstract
A novel method for the preparation of highly functionalized 4-oxo-3-(1H-pyrrol-3-yl)-4H-chromenes (OPCMs) from 3-formylchromones and α-isocyanoacetates via an unprecedented three-component [1 + 1 + 3] cycloaddition reaction in one pot was developed. The three-component cascade reaction was enabled by refluxing a mixture of the substrates in 1,4-dioxane in the presence of Ag2CO3 as a Lewis acid promoter. As a result, a series of functionalized pyrroles (OPCMs, 3), was prepared regioselectively and in high yields (80%–88%) through the formation of three bonds. This protocol can be used in the synthesis of OPCMs rather than through conventional, multi-step reactions and is suitable for both combinatorial and parallel syntheses of pyrroles.
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