{"title":"Synthesis of 2-(Trifluoromethyl)Azetidines by Strain-Release Reactions of 2-(Trifluoromethyl)-1-Azabicyclo[1.1.0]Butanes","authors":"Anaïs Scuiller, Alexandre Dupas, Gauthier Lefebvre, Naïssa Bouriche, Henri Chédotal, Gérard Guillamot, Janine Cossy, Christophe Meyer","doi":"10.1002/chem.202500590","DOIUrl":null,"url":null,"abstract":"<p>Substituted azetidines are privileged heterocyclic scaffolds in medicinal chemistry and have become synthetic targets of high interest in recent years. With the goal of developing a new access to azetidines incorporating the pharmaceutically relevant trifluoromethyl group, the reactivity of 2-(trifluoromethyl)-1-azabicyclo[1.1.0]butanes was investigated in polar strain-release reactions. By using benzyl chloroformate or trifluoroacetic anhydride as reacting partners, diversely substituted 3-chloroazetidines, 3-substituted azetidines and azetidin-3-ols bearing a trifluoromethyl group at C2 could be readily synthesized. In addition, palladium-catalyzed hydrogenolysis reactions provided an entry to <i>cis-</i>3-aryl-2-trifluoromethyl azetidines.</p>","PeriodicalId":144,"journal":{"name":"Chemistry - A European Journal","volume":"31 29","pages":""},"PeriodicalIF":3.7000,"publicationDate":"2025-04-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/chem.202500590","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemistry - A European Journal","FirstCategoryId":"92","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/chem.202500590","RegionNum":2,"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
Substituted azetidines are privileged heterocyclic scaffolds in medicinal chemistry and have become synthetic targets of high interest in recent years. With the goal of developing a new access to azetidines incorporating the pharmaceutically relevant trifluoromethyl group, the reactivity of 2-(trifluoromethyl)-1-azabicyclo[1.1.0]butanes was investigated in polar strain-release reactions. By using benzyl chloroformate or trifluoroacetic anhydride as reacting partners, diversely substituted 3-chloroazetidines, 3-substituted azetidines and azetidin-3-ols bearing a trifluoromethyl group at C2 could be readily synthesized. In addition, palladium-catalyzed hydrogenolysis reactions provided an entry to cis-3-aryl-2-trifluoromethyl azetidines.
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Chemistry—A European Journal is a truly international journal with top quality contributions (2018 ISI Impact Factor: 5.16). It publishes a wide range of outstanding Reviews, Minireviews, Concepts, Full Papers, and Communications from all areas of chemistry and related fields.
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