1-硝基甲基四氢异喹啉衍生物的串联C-H键氧化/C-N键裂解/[3+2]环加成：多功能化异恶唑和异恶唑啉骨架的构建。

IF 3.6 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-02-14 Epub Date: 2025-01-31 DOI:10.1021/acs.joc.4c03048

Yuhao Zhu, Jie Mao, Qiyuan Ma, Shuwei Zhang, Yu Yuan, Xiaodong Jia

{"title":"1-硝基甲基四氢异喹啉衍生物的串联C-H键氧化/C-N键裂解/[3+2]环加成：多功能化异恶唑和异恶唑啉骨架的构建。","authors":"Yuhao Zhu, Jie Mao, Qiyuan Ma, Shuwei Zhang, Yu Yuan, Xiaodong Jia","doi":"10.1021/acs.joc.4c03048","DOIUrl":null,"url":null,"abstract":"A TBN-enabled tandem C-H bond oxidation/C-N bond cleavage/[3+2] cycloaddition of 1-nitromethyltetrahydroisoquinolines was realized, constructing a series of multifunctionalized isoxazole and isoxazoline skeletons in the presence of alkynes and alkenes, respectively. Various functional groups were smoothly tolerated, and the mechanistic study revealed that the construction of isoxazole and isoxazoline rings is mediated by the in situ generated nitrile oxides.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":" ","pages":"2459-2471"},"PeriodicalIF":3.6000,"publicationDate":"2025-02-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"tert-Butyl Nitrite (TBN)-Enabled Tandem C-H Bond Oxidation/C-N Bond Cleavage/[3+2] Cycloaddition of 1-Nitromethyltetrahydroisoquinoline Derivatives: Construction of Multifunctionalized Isoxazole and Isoxazoline Skeletons.\",\"authors\":\"Yuhao Zhu, Jie Mao, Qiyuan Ma, Shuwei Zhang, Yu Yuan, Xiaodong Jia\",\"doi\":\"10.1021/acs.joc.4c03048\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"A TBN-enabled tandem C-H bond oxidation/C-N bond cleavage/[3+2] cycloaddition of 1-nitromethyltetrahydroisoquinolines was realized, constructing a series of multifunctionalized isoxazole and isoxazoline skeletons in the presence of alkynes and alkenes, respectively. Various functional groups were smoothly tolerated, and the mechanistic study revealed that the construction of isoxazole and isoxazoline rings is mediated by the in situ generated nitrile oxides.\",\"PeriodicalId\":57,\"journal\":{\"name\":\"Journal of Organic Chemistry\",\"volume\":\" \",\"pages\":\"2459-2471\"},\"PeriodicalIF\":3.6000,\"publicationDate\":\"2025-02-14\",\"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.4c03048\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2025/1/31 0:00:00\",\"PubModel\":\"Epub\",\"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.4c03048","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/1/31 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}

引用次数: 0

摘要

在炔烃和烯烃的存在下，实现了 TBN 支持的 1-硝基甲基四氢异喹啉的串联 C-H 键氧化/C-N 键裂解/[3+2] 环加成，分别构建了一系列多功能化异噁唑和异噁唑啉骨架。机理研究表明，异噁唑和异噁唑啉环的构建是由原位生成的腈氧化物介导的。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

tert-Butyl Nitrite (TBN)-Enabled Tandem C-H Bond Oxidation/C-N Bond Cleavage/[3+2] Cycloaddition of 1-Nitromethyltetrahydroisoquinoline Derivatives: Construction of Multifunctionalized Isoxazole and Isoxazoline Skeletons.

查看原文本刊更多论文

tert-Butyl Nitrite (TBN)-Enabled Tandem C-H Bond Oxidation/C-N Bond Cleavage/[3+2] Cycloaddition of 1-Nitromethyltetrahydroisoquinoline Derivatives: Construction of Multifunctionalized Isoxazole and Isoxazoline Skeletons.

A TBN-enabled tandem C-H bond oxidation/C-N bond cleavage/[3+2] cycloaddition of 1-nitromethyltetrahydroisoquinolines was realized, constructing a series of multifunctionalized isoxazole and isoxazoline skeletons in the presence of alkynes and alkenes, respectively. Various functional groups were smoothly tolerated, and the mechanistic study revealed that the construction of isoxazole and isoxazoline rings is mediated by the in situ generated nitrile oxides.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

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.