以二甲基亚砜为C1源，K2S2O8/ tfa介导[3+2+1]苯胺和醇合成取代喹啉

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters Pub Date : 2025-06-28 DOI:10.1016/j.tetlet.2025.155724

Zhipin Wang, Zheng Li

{"title":"以二甲基亚砜为C1源，K2S2O8/ tfa介导[3+2+1]苯胺和醇合成取代喹啉","authors":"Zhipin Wang, Zheng Li","doi":"10.1016/j.tetlet.2025.155724","DOIUrl":null,"url":null,"abstract":"<div><div>An efficient K<sub>2</sub>S<sub>2</sub>O<sub>8</sub>/TFA-mediated [3+2+1] cycloadditions of readily available anilines, primary alcohols/secondary alcohols, and DMSO is described. This method allows the direct and highly effective synthesis of privileged quinolones, such as 3-arylquinolines and 4-arylquinolines, with exclusive regioselectivity and good functional group tolerance in good to excellent yield. DMSO is employed as the C1 building block of quinoline products, the oxidant, and the solvent. The possible reaction mechanism is also discussed. The method can also be extended to a gram scale.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"168 ","pages":"Article 155724"},"PeriodicalIF":1.5000,"publicationDate":"2025-06-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"K2S2O8/TFA-mediated [3+2+1] synthesis of substituted quinolines from anilines and alcohols using DMSO as a C1 source\",\"authors\":\"Zhipin Wang, Zheng Li\",\"doi\":\"10.1016/j.tetlet.2025.155724\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>An efficient K<sub>2</sub>S<sub>2</sub>O<sub>8</sub>/TFA-mediated [3+2+1] cycloadditions of readily available anilines, primary alcohols/secondary alcohols, and DMSO is described. This method allows the direct and highly effective synthesis of privileged quinolones, such as 3-arylquinolines and 4-arylquinolines, with exclusive regioselectivity and good functional group tolerance in good to excellent yield. DMSO is employed as the C1 building block of quinoline products, the oxidant, and the solvent. The possible reaction mechanism is also discussed. The method can also be extended to a gram scale.</div></div>\",\"PeriodicalId\":438,\"journal\":{\"name\":\"Tetrahedron Letters\",\"volume\":\"168 \",\"pages\":\"Article 155724\"},\"PeriodicalIF\":1.5000,\"publicationDate\":\"2025-06-28\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Tetrahedron Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0040403925002734\",\"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":"Tetrahedron Letters","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040403925002734","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}

引用次数: 0

摘要

描述了一种高效的K2S2O8/ tfa介导的苯胺，伯醇/仲醇和DMSO的[3+2+1]环加成反应。该方法可直接高效合成3-芳基喹啉类和4-芳基喹啉类特权喹诺酮类化合物，具有专一的区域选择性和良好的官能团耐受性，收率高。二甲基亚砜被用作喹啉产品的C1构建块、氧化剂和溶剂。并对可能的反应机理进行了讨论。该方法也可以扩展到克尺度。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

K2S2O8/TFA-mediated [3+2+1] synthesis of substituted quinolines from anilines and alcohols using DMSO as a C1 source

查看原文本刊更多论文

K2S2O8/TFA-mediated [3+2+1] synthesis of substituted quinolines from anilines and alcohols using DMSO as a C1 source

An efficient K₂S₂O₈/TFA-mediated [3+2+1] cycloadditions of readily available anilines, primary alcohols/secondary alcohols, and DMSO is described. This method allows the direct and highly effective synthesis of privileged quinolones, such as 3-arylquinolines and 4-arylquinolines, with exclusive regioselectivity and good functional group tolerance in good to excellent yield. DMSO is employed as the C1 building block of quinoline products, the oxidant, and the solvent. The possible reaction mechanism is also discussed. The method can also be extended to a gram scale.

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

Tetrahedron Letters 化学-有机化学

CiteScore

3.50

自引率

5.60%

发文量

521

审稿时长

28 days

期刊介绍： Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.