三组分环加成制备异恶唑-熔接呋喃[3,2-b]喹啉

IF 2.5 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry Pub Date : 2025-05-21 DOI:10.1002/ejoc.202500007

Chun‐Yu Nong , Xiu‐Qing Mo , Jin‐He Zhao , Lu Lei , Lu Ma , Prof. Dong‐Liang Mo

{"title":"三组分环加成制备异恶唑-熔接呋喃[3,2-b]喹啉","authors":"Chun‐Yu Nong , Xiu‐Qing Mo , Jin‐He Zhao , Lu Lei , Lu Ma , Prof. Dong‐Liang Mo","doi":"10.1002/ejoc.202500007","DOIUrl":null,"url":null,"abstract":"<div><div>A variety of isooxazoline‐fused furo[3,2‐b]quinolines containing four stereocenters were prepared in 40 %‐87 % yields with high regioselectivity and diastereoselectivity. The control experimental results revealed that the reaction underwent in the order of [4+2] cycloaddition and sequential [3+2] cycloaddition between aza‐<em>ortho</em>‐quinone methides (ao‐QM) generated from 2‐chloromethyl anilines, furans, and nitrile <em>N</em>‐oxides generated from hydroxamoyl chlorides. The present method features mild reaction conditions, broad substrate scope, high diastereoselectivity of four stereocenters, and novel scaffolds of isooxazoline‐fused furo[3,2‐b]quinolines.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 17","pages":"Article e202500007"},"PeriodicalIF":2.5000,"publicationDate":"2025-05-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Three‐Component Cycloadditions to Prepare Isooxazoline‐Fused Furo[3,2‐b]quinolines\",\"authors\":\"Chun‐Yu Nong , Xiu‐Qing Mo , Jin‐He Zhao , Lu Lei , Lu Ma , Prof. Dong‐Liang Mo\",\"doi\":\"10.1002/ejoc.202500007\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>A variety of isooxazoline‐fused furo[3,2‐b]quinolines containing four stereocenters were prepared in 40 %‐87 % yields with high regioselectivity and diastereoselectivity. The control experimental results revealed that the reaction underwent in the order of [4+2] cycloaddition and sequential [3+2] cycloaddition between aza‐<em>ortho</em>‐quinone methides (ao‐QM) generated from 2‐chloromethyl anilines, furans, and nitrile <em>N</em>‐oxides generated from hydroxamoyl chlorides. The present method features mild reaction conditions, broad substrate scope, high diastereoselectivity of four stereocenters, and novel scaffolds of isooxazoline‐fused furo[3,2‐b]quinolines.</div></div>\",\"PeriodicalId\":167,\"journal\":{\"name\":\"European Journal of Organic Chemistry\",\"volume\":\"28 17\",\"pages\":\"Article e202500007\"},\"PeriodicalIF\":2.5000,\"publicationDate\":\"2025-05-21\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"European Journal of Organic Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S1434193X25001641\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"European Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1434193X25001641","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}

引用次数: 0

摘要

以高区域选择性和非对映选择性为条件，以40% ~ 87%的收率制备了多种含有四个立体中心的异唑啉-融合呋喃[3,2-b]喹啉。对照实验结果表明，2-氯甲基苯胺生成的偶氮-邻醌类化合物（ao-QM）、呋喃生成的偶氮-邻醌类化合物（ao-QM）、羟戊酰氯生成的腈n -氧化物生成的偶氮-邻醌类化合物（ao-QM）依次发生了[4+2]环加成和[3+2]环加成反应。该方法具有反应条件温和、底物范围广、四个立体中心的非对映选择性高、异恶唑-融合呋喃[3,2-b]喹啉类化合物的新型支架等特点。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

查看原文本刊更多论文

Three‐Component Cycloadditions to Prepare Isooxazoline‐Fused Furo[3,2‐b]quinolines

A variety of isooxazoline‐fused furo[3,2‐b]quinolines containing four stereocenters were prepared in 40 %‐87 % yields with high regioselectivity and diastereoselectivity. The control experimental results revealed that the reaction underwent in the order of [4+2] cycloaddition and sequential [3+2] cycloaddition between aza‐ortho‐quinone methides (ao‐QM) generated from 2‐chloromethyl anilines, furans, and nitrile N‐oxides generated from hydroxamoyl chlorides. The present method features mild reaction conditions, broad substrate scope, high diastereoselectivity of four stereocenters, and novel scaffolds of isooxazoline‐fused furo[3,2‐b]quinolines.

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

European Journal of Organic Chemistry 化学-有机化学

CiteScore

5.40

自引率

3.60%

发文量

752

审稿时长

1 months

期刊介绍： The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry: Liebigs Annalen Bulletin des Sociétés Chimiques Belges Bulletin de la Société Chimique de France Gazzetta Chimica Italiana Recueil des Travaux Chimiques des Pays-Bas Anales de Química Chimika Chronika Revista Portuguesa de Química ACH—Models in Chemistry Polish Journal of Chemistry.