{"title":"Ring-Opening Chlorination and Bromination of Pyrazolopyridines and Isoxazoles","authors":"Hugo Ohki, Prof. Dr. Junichiro Yamaguchi","doi":"10.1002/chem.202501589","DOIUrl":null,"url":null,"abstract":"<p>We report the development of electrophilic ring-opening chlorination and bromination reactions of pyrazoloazines and isoxazoles using chlorinating and brominating agents. These transformations proceed via selective cleavage of heteroaromatic N─N or N─O bonds, delivering structurally diverse tertiary halogenated compounds. Furthermore, treatment of formylated pyrazolopyridines with two equivalents of chlorinating or brominating agents afforded dihalogenated products in good yields. This strategy represents a valuable platform for constructing halogenated scaffolds from simple heteroaromatic precursors and broadens the synthetic utility of skeletal transformations in the functionalization of heteroaromatics.</p>","PeriodicalId":144,"journal":{"name":"Chemistry - A European Journal","volume":"31 41","pages":""},"PeriodicalIF":3.7000,"publicationDate":"2025-07-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/chem.202501589","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemistry - A European Journal","FirstCategoryId":"92","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/chem.202501589","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
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Abstract
We report the development of electrophilic ring-opening chlorination and bromination reactions of pyrazoloazines and isoxazoles using chlorinating and brominating agents. These transformations proceed via selective cleavage of heteroaromatic N─N or N─O bonds, delivering structurally diverse tertiary halogenated compounds. Furthermore, treatment of formylated pyrazolopyridines with two equivalents of chlorinating or brominating agents afforded dihalogenated products in good yields. This strategy represents a valuable platform for constructing halogenated scaffolds from simple heteroaromatic precursors and broadens the synthetic utility of skeletal transformations in the functionalization of heteroaromatics.
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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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