{"title":"CsF-mediated reaction of diazo compounds with 3-nitroindoles: access to cyano- and phosphonylpyrazolo[4,3-b]indoles†","authors":"Sandeep Kumar, Ashis Kumar Gupta, Narendra Kumar Vaishanv, Ruchir Kant and Kishor Mohanan","doi":"10.1039/D4NJ03266G","DOIUrl":null,"url":null,"abstract":"<p >A CsF-promoted synthesis of cyanopyrazolo[4,3-<em>b</em>]indoles <em>via</em> a [3+2] cycloaddition reaction of diazoacetonitrile with <em>N</em>-substituted 3-nitroindoles and subsequent elimination of the nitro group has been devised. This protocol delivers diverse cyano-containing pyrazole-fused indoles in good to excellent yields under mild conditions. Besides diazoacetonitrile, the Seyferth–Gilbert reagent (SGR) readily participated in this reaction to provide facile access to phosphonylated pyrazolo[4,3-<em>b</em>]indoles.</p>","PeriodicalId":95,"journal":{"name":"New Journal of Chemistry","volume":null,"pages":null},"PeriodicalIF":2.7000,"publicationDate":"2024-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"New Journal of Chemistry","FirstCategoryId":"92","ListUrlMain":"https://pubs.rsc.org/en/content/articlelanding/2024/nj/d4nj03266g","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
A CsF-promoted synthesis of cyanopyrazolo[4,3-b]indoles via a [3+2] cycloaddition reaction of diazoacetonitrile with N-substituted 3-nitroindoles and subsequent elimination of the nitro group has been devised. This protocol delivers diverse cyano-containing pyrazole-fused indoles in good to excellent yields under mild conditions. Besides diazoacetonitrile, the Seyferth–Gilbert reagent (SGR) readily participated in this reaction to provide facile access to phosphonylated pyrazolo[4,3-b]indoles.