{"title":"N-Benzyl-propiolamides 的碘化制备，生成氮杂螺[5.5]十一烷三烯酮或苯并[c]氮杂卓酮","authors":"Chada Raji Reddy, Thallamapuram Nagendraprasad, Jannatul Islam, Uprety Ajaykumar, Cirandur Suresh Reddy, Srivari Chandrasekhar","doi":"10.1055/a-2349-6736","DOIUrl":null,"url":null,"abstract":"<p>Iodine-mediated oxidative annulations of <i>N</i>-benzyl-propiolamides are disclosed for the first time, providing either azaspiro[5.5]undecatrienones via dearomative <i>ipso</i>-annulation or benzo[<i>c</i>]azepinones through <i>ortho</i>-annulation. The selective construction of the aforementioned products is based on the ceric ammonium nitrate (CAN)-promoted divergent reactivity of the propiolamide, directed by the substituents on the phenyl ring of the <i>N</i>-benzyl group.</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0000,"publicationDate":"2024-07-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Iodo-Annulations of N-Benzyl-propiolamides Leading To Azaspiro[5.5]undecatrienones or Benzo[c]azepinones\",\"authors\":\"Chada Raji Reddy, Thallamapuram Nagendraprasad, Jannatul Islam, Uprety Ajaykumar, Cirandur Suresh Reddy, Srivari Chandrasekhar\",\"doi\":\"10.1055/a-2349-6736\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p>Iodine-mediated oxidative annulations of <i>N</i>-benzyl-propiolamides are disclosed for the first time, providing either azaspiro[5.5]undecatrienones via dearomative <i>ipso</i>-annulation or benzo[<i>c</i>]azepinones through <i>ortho</i>-annulation. The selective construction of the aforementioned products is based on the ceric ammonium nitrate (CAN)-promoted divergent reactivity of the propiolamide, directed by the substituents on the phenyl ring of the <i>N</i>-benzyl group.</p> \",\"PeriodicalId\":501298,\"journal\":{\"name\":\"Synthesis\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2024-07-15\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Synthesis\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.1055/a-2349-6736\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synthesis","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1055/a-2349-6736","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
Iodo-Annulations of N-Benzyl-propiolamides Leading To Azaspiro[5.5]undecatrienones or Benzo[c]azepinones
Iodine-mediated oxidative annulations of N-benzyl-propiolamides are disclosed for the first time, providing either azaspiro[5.5]undecatrienones via dearomative ipso-annulation or benzo[c]azepinones through ortho-annulation. The selective construction of the aforementioned products is based on the ceric ammonium nitrate (CAN)-promoted divergent reactivity of the propiolamide, directed by the substituents on the phenyl ring of the N-benzyl group.
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