{"title":"n -甲基腙的分离:n -氰基甲基腙的合成及其[3,3]-异位重排至2-氨基咪唑","authors":"Yiwen Xia, Meng Tang","doi":"10.1021/acs.joc.4c02580","DOIUrl":null,"url":null,"abstract":"The umpolung of <i>N</i>-tosylhydrazones was reported for the first time. Synthesis of <i>N</i>-cyano tosylhydrazones was developed, and various <i>N</i>-cyano tosylhydrazones were prepared in good yields. An umpolung <i>N</i>-tosylhydrazones mechanism was proposed. Meanwhile, the [3,3]-sigmatropic rearrangement of <i>N</i>-cyano tosylhydrazones was examined, and the corresponding 2-aminoimidazoles were given.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"262 1","pages":""},"PeriodicalIF":3.6000,"publicationDate":"2024-12-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Umpolung of N-Tosylhydrazones: Synthesis of N-Cyano Tosylhydrazones and Their [3,3]-Sigmatropic Rearrangement to 2-Aminoimidazoles\",\"authors\":\"Yiwen Xia, Meng Tang\",\"doi\":\"10.1021/acs.joc.4c02580\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"The umpolung of <i>N</i>-tosylhydrazones was reported for the first time. Synthesis of <i>N</i>-cyano tosylhydrazones was developed, and various <i>N</i>-cyano tosylhydrazones were prepared in good yields. An umpolung <i>N</i>-tosylhydrazones mechanism was proposed. Meanwhile, the [3,3]-sigmatropic rearrangement of <i>N</i>-cyano tosylhydrazones was examined, and the corresponding 2-aminoimidazoles were given.\",\"PeriodicalId\":57,\"journal\":{\"name\":\"Journal of Organic Chemistry\",\"volume\":\"262 1\",\"pages\":\"\"},\"PeriodicalIF\":3.6000,\"publicationDate\":\"2024-12-03\",\"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.4c02580\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.4c02580","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
摘要
n -甲酰基腙的检测为首次报道。研究了n -氰基甲酰腙的合成方法,并以较好的收率制备了多种n -氰基甲酰腙。提出了一种n -羟基腙的非极化机理。同时,考察了n -氰基甲苯腙的[3,3]-异位重排,并给出了相应的2-氨基咪唑。
Umpolung of N-Tosylhydrazones: Synthesis of N-Cyano Tosylhydrazones and Their [3,3]-Sigmatropic Rearrangement to 2-Aminoimidazoles
The umpolung of N-tosylhydrazones was reported for the first time. Synthesis of N-cyano tosylhydrazones was developed, and various N-cyano tosylhydrazones were prepared in good yields. An umpolung N-tosylhydrazones mechanism was proposed. Meanwhile, the [3,3]-sigmatropic rearrangement of N-cyano tosylhydrazones was examined, and the corresponding 2-aminoimidazoles were given.
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.