{"title":"Access to Methylidene-Azaspiro[4.5]decatrienones via Radical-Promoted Domino Thio-Functionalization/Dearomative Ipso-Annulation","authors":"Chada Raji Reddy, Puthiya Purayil Vinaya, Ejjirotu Srinivasu, Muppidi Subbarao","doi":"10.1021/acs.joc.5c00077","DOIUrl":null,"url":null,"abstract":"An unprecedented approach involving radical-mediated sulfonylation/dearomative <i>ipso</i>-annulation of <i>N</i>-(methyl-2-phenylacetate)propiolamides using arylsulfonyl radical, generated from aryl diazonium salt in the presence of DABSO, is developed. This strategy provides uniquely substituted 3-sulfonyl <i>aza</i>spiro[4.5]decatrienones in good yields. The developed approach has also been extended fruitfully to 3-thiocyano <i>aza</i>-spirocycles through domino thiocyanation/dearomative <i>ipso</i>-annulation.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"91 1","pages":""},"PeriodicalIF":3.6000,"publicationDate":"2025-04-09","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.5c00077","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
An unprecedented approach involving radical-mediated sulfonylation/dearomative ipso-annulation of N-(methyl-2-phenylacetate)propiolamides using arylsulfonyl radical, generated from aryl diazonium salt in the presence of DABSO, is developed. This strategy provides uniquely substituted 3-sulfonyl azaspiro[4.5]decatrienones in good yields. The developed approach has also been extended fruitfully to 3-thiocyano aza-spirocycles through domino thiocyanation/dearomative ipso-annulation.
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.
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