{"title":"Regioselective 5-exo-dig (halo)cyclization of N-propargyloxycarbonyl guanidine derivatives under mild conditions†","authors":"Bohong Lin, Yaoping Ruan, Qi Hou, Zhijun Yuan, Yunshi Liang and Jing Zhang","doi":"10.1039/D4OB00579A","DOIUrl":null,"url":null,"abstract":"<p >A highly regioselective 5-<em>exo-dig</em> cyclization of aromatic <em>N</em>-propargyloxycarbonyl guanidines was developed <em>via</em> an Ag(<small>I</small>)-catalyzed intramolecular hydroamination reaction. This method features a fast reaction rate and mild reaction conditions. Furthermore, it was extended to access halogenated analogues <em>via</em> a one-pot Ag(<small>I</small>)-catalyzed bromocyclization reaction or an I<small><sub>2</sub></small>-mediated iodocyclization reaction with high <em>E</em>/<em>Z</em> selectivity.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9000,"publicationDate":"2024-06-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://pubs.rsc.org/en/content/articlelanding/2024/ob/d4ob00579a","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
A highly regioselective 5-exo-dig cyclization of aromatic N-propargyloxycarbonyl guanidines was developed via an Ag(I)-catalyzed intramolecular hydroamination reaction. This method features a fast reaction rate and mild reaction conditions. Furthermore, it was extended to access halogenated analogues via a one-pot Ag(I)-catalyzed bromocyclization reaction or an I2-mediated iodocyclization reaction with high E/Z selectivity.
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