{"title":"PIFA 介导的 2-氨基喹喔啉分子内 N-芳基化反应生成吲哚并[2,3-b]喹喔啉衍生物。","authors":"","doi":"10.1039/d4ob00812j","DOIUrl":null,"url":null,"abstract":"<div><p>We present the PIFA-mediated intramolecular <em>N</em>-arylation of 2-aminoquinoxalines at room temperature for the first time. This method provides a wide range of indolo[2,3-<em>b</em>]quinoxalines in good to excellent yields within a short time. The C–H bond functionalization occurs without the need for an inert atmosphere or additives. Additionally, a double C–H bond functionalization was observed, where the first reaction forms a C–N bond (<em>N</em>-arylation) and the second forms a C–O bond, yielding an acetal-functionalized product. Mechanistic investigations suggest that the C–H bond functionalization proceeds through an ionic mechanism, whereas acetal functionalization follows a radical pathway. This method extends to the derivation of indoloquinoxalines, including the target compound BIQMCz.</p></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9000,"publicationDate":"2024-07-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"PIFA-mediated intramolecular N-arylation of 2-aminoquinoxalines to afford indolo[2,3-b]quinoxaline derivatives†\",\"authors\":\"\",\"doi\":\"10.1039/d4ob00812j\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>We present the PIFA-mediated intramolecular <em>N</em>-arylation of 2-aminoquinoxalines at room temperature for the first time. This method provides a wide range of indolo[2,3-<em>b</em>]quinoxalines in good to excellent yields within a short time. The C–H bond functionalization occurs without the need for an inert atmosphere or additives. Additionally, a double C–H bond functionalization was observed, where the first reaction forms a C–N bond (<em>N</em>-arylation) and the second forms a C–O bond, yielding an acetal-functionalized product. Mechanistic investigations suggest that the C–H bond functionalization proceeds through an ionic mechanism, whereas acetal functionalization follows a radical pathway. This method extends to the derivation of indoloquinoxalines, including the target compound BIQMCz.</p></div>\",\"PeriodicalId\":96,\"journal\":{\"name\":\"Organic & Biomolecular Chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":2.9000,\"publicationDate\":\"2024-07-17\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic & Biomolecular Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S1477052024005743\",\"RegionNum\":3,\"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":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1477052024005743","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
PIFA-mediated intramolecular N-arylation of 2-aminoquinoxalines to afford indolo[2,3-b]quinoxaline derivatives†
We present the PIFA-mediated intramolecular N-arylation of 2-aminoquinoxalines at room temperature for the first time. This method provides a wide range of indolo[2,3-b]quinoxalines in good to excellent yields within a short time. The C–H bond functionalization occurs without the need for an inert atmosphere or additives. Additionally, a double C–H bond functionalization was observed, where the first reaction forms a C–N bond (N-arylation) and the second forms a C–O bond, yielding an acetal-functionalized product. Mechanistic investigations suggest that the C–H bond functionalization proceeds through an ionic mechanism, whereas acetal functionalization follows a radical pathway. This method extends to the derivation of indoloquinoxalines, including the target compound BIQMCz.