Lu Yin, Zhou Zhang, Shuntao Huang, Zhuoyu Wang, Chao Huang
{"title":"Brønsted Acid Triggers [6/7 + 1] Cascade Cyclization by <i>N</i>-Alkyl Amine C(sp<sup>3</sup>)-N Cleavage: Mild Synthesis of Benzo[1,4]oxazepane and Dihydrobenzo[1,5]oxazocine.","authors":"Lu Yin, Zhou Zhang, Shuntao Huang, Zhuoyu Wang, Chao Huang","doi":"10.1021/acs.joc.4c01827","DOIUrl":null,"url":null,"abstract":"<p><p>A catalyst-free mild synthesis was reported to produce medium-ring oxazepane and oxazocine derivatives from aminomaleimides and <i>N</i>-alkyl amines. The substrate and acidic additives were employed to cleave the C(sp<sup>3</sup>)-N bond as a one-carbon synthon for C-C and C-O coupling, thus facilitating the [<i>n</i> + 1] cascade cyclization reaction, which enabled the construction of seven- and eight-membered <i>N</i>,<i>O</i>-heterocycles at room temperature. The method exhibits abroad substrate scope and remarkable tolerance toward various functional groups (seven-membered 28 examples, eight-membered 8 examples, and activated <i>N</i>-alkyl amine 12 examples) and utilization of natural products (2 examples).</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3000,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"The Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.4c01827","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/9/1 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
A catalyst-free mild synthesis was reported to produce medium-ring oxazepane and oxazocine derivatives from aminomaleimides and N-alkyl amines. The substrate and acidic additives were employed to cleave the C(sp3)-N bond as a one-carbon synthon for C-C and C-O coupling, thus facilitating the [n + 1] cascade cyclization reaction, which enabled the construction of seven- and eight-membered N,O-heterocycles at room temperature. The method exhibits abroad substrate scope and remarkable tolerance toward various functional groups (seven-membered 28 examples, eight-membered 8 examples, and activated N-alkyl amine 12 examples) and utilization of natural products (2 examples).
期刊介绍:
The 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.