Andrey R. Galeev, Maksim V. Dmitriev, Alexander S. Novikov, Andrey N. Maslivets
{"title":"Heterocycle-guided synthesis of m-hetarylanilines via three-component benzannulation","authors":"Andrey R. Galeev, Maksim V. Dmitriev, Alexander S. Novikov, Andrey N. Maslivets","doi":"10.3762/bjoc.20.188","DOIUrl":null,"url":null,"abstract":"<p><font size='+1'><b>Abstract</b></font></p>\n<p>A one-pot three-component synthesis of substituted <i>meta</i>-hetarylanilines from heterocycle-substituted 1,3-diketones has been developed. The electron-withdrawing power of the heterocyclic substituent (which can be estimated on the basis of calculated Hammett constants) in the 1,3-diketone plays a pivotal role in the studied reaction. The series of <i>meta</i>-hetarylanilines prepared (21–85% isolated yield) demonstrates the synthetic utility of the developed method.</p>\n<p align='center'><img src='https://www.beilstein-journals.org/bjoc/content/figures/1860-5397-20-188-graphical-abstract.png?max-width=550' border='0'/></p>\n<p><i>Beilstein J. Org. Chem.</i> <b>2024,</b> <i>20,</i> 2208–2216. doi:10.3762/bjoc.20.188</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"11 1","pages":""},"PeriodicalIF":2.2000,"publicationDate":"2024-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Beilstein Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.3762/bjoc.20.188","RegionNum":4,"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
Abstract
A one-pot three-component synthesis of substituted meta-hetarylanilines from heterocycle-substituted 1,3-diketones has been developed. The electron-withdrawing power of the heterocyclic substituent (which can be estimated on the basis of calculated Hammett constants) in the 1,3-diketone plays a pivotal role in the studied reaction. The series of meta-hetarylanilines prepared (21–85% isolated yield) demonstrates the synthetic utility of the developed method.
Beilstein J. Org. Chem.2024,20, 2208–2216. doi:10.3762/bjoc.20.188
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