{"title":"Synthesis of SeCF<sub>3</sub>-Substituted Oxazines and Oxazolines through Electrophilic Trifluoromethylselenolation Cyclization of Propargylic Amides.","authors":"Jia Wang, Jia-Qi Niu, Jia-Cheng Li, Lixia Liu, Xuefang Shang, Ping-Xin Zhou, Shujun Chao","doi":"10.1021/acs.joc.5c00930","DOIUrl":null,"url":null,"abstract":"<p><p>The electrophilic trifluoromethylselenolation cyclizations of propargylic amides are disclosed. The transformations undergo the 6-<i>endo</i>-dig and 5-<i>exo</i>-dig cyclizations to synthesize SeCF<sub>3</sub>-substituted oxazines and oxazolines, respectively, which are induced by <i>N</i>-trifluoromethylselenophthalimide. This protocol is suitable for late-stage applications of complex natural products and drug molecules.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":3.3000,"publicationDate":"2025-06-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.5c00930","RegionNum":2,"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
The electrophilic trifluoromethylselenolation cyclizations of propargylic amides are disclosed. The transformations undergo the 6-endo-dig and 5-exo-dig cyclizations to synthesize SeCF3-substituted oxazines and oxazolines, respectively, which are induced by N-trifluoromethylselenophthalimide. This protocol is suitable for late-stage applications of complex natural products and drug molecules.
期刊介绍:
Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.