{"title":"通过[1,4]-肼转移形成苯并[7]萘衍生物的(n+3)-环化：涉及内部氧化还原反应的新型环化模式","authors":"Jun Nagaki, Tomoko Kawasaki-Takasuka, Keiji Mori","doi":"10.1055/a-2287-9391","DOIUrl":null,"url":null,"abstract":"<p>We report a unique synthetic route to benzo[7]annulene derivatives. When benzylidene malonates having a 1-(<i>N</i>,<i>N</i>-dialkylamino)alkyl group at the <i>ortho</i>-position are treated with a stoichiometric amount of M(OTf)<sub>3</sub> (M = Sc, Yb, Gd), three transformations ([1,4]-hydride shift/isomerization into an enamine/intramolecular Stork enamine acylation) proceed sequentially to afford various benzo[7]annulene derivatives in moderate chemical yields. To our knowledge, the present reaction is the first example of an internal redox reaction involving a [1,<i>n</i>]-hydride shift/(<i>n</i>+3)-cyclization process.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"45 1","pages":""},"PeriodicalIF":1.7000,"publicationDate":"2024-04-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"(n+3)-Cyclization for the Formation of Benzo[7]annulene Derivatives via a [1,4]-Hydride Shift: A Novel Cyclization Mode Involving an Internal Redox Reaction\",\"authors\":\"Jun Nagaki, Tomoko Kawasaki-Takasuka, Keiji Mori\",\"doi\":\"10.1055/a-2287-9391\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p>We report a unique synthetic route to benzo[7]annulene derivatives. When benzylidene malonates having a 1-(<i>N</i>,<i>N</i>-dialkylamino)alkyl group at the <i>ortho</i>-position are treated with a stoichiometric amount of M(OTf)<sub>3</sub> (M = Sc, Yb, Gd), three transformations ([1,4]-hydride shift/isomerization into an enamine/intramolecular Stork enamine acylation) proceed sequentially to afford various benzo[7]annulene derivatives in moderate chemical yields. To our knowledge, the present reaction is the first example of an internal redox reaction involving a [1,<i>n</i>]-hydride shift/(<i>n</i>+3)-cyclization process.</p> \",\"PeriodicalId\":22319,\"journal\":{\"name\":\"Synlett\",\"volume\":\"45 1\",\"pages\":\"\"},\"PeriodicalIF\":1.7000,\"publicationDate\":\"2024-04-04\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Synlett\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1055/a-2287-9391\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synlett","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1055/a-2287-9391","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
(n+3)-Cyclization for the Formation of Benzo[7]annulene Derivatives via a [1,4]-Hydride Shift: A Novel Cyclization Mode Involving an Internal Redox Reaction
We report a unique synthetic route to benzo[7]annulene derivatives. When benzylidene malonates having a 1-(N,N-dialkylamino)alkyl group at the ortho-position are treated with a stoichiometric amount of M(OTf)3 (M = Sc, Yb, Gd), three transformations ([1,4]-hydride shift/isomerization into an enamine/intramolecular Stork enamine acylation) proceed sequentially to afford various benzo[7]annulene derivatives in moderate chemical yields. To our knowledge, the present reaction is the first example of an internal redox reaction involving a [1,n]-hydride shift/(n+3)-cyclization process.
期刊介绍：
SYNLETT is an international journal reporting research results and current trends in chemical synthesis in short personalized reviews and preliminary communications. It covers all fields of scientific endeavor that involve organic synthesis, including catalysis, organometallic, medicinal, biological, and photochemistry, but also related disciplines and offers the possibility to publish scientific primary data.
京公网安备 11010802042870号
京ICP备2023020795号-1
分享
求助内容：
应助结果提醒方式：
扫码关注我们
