Di Hao , Zhen Yang , Luigi Vaccaro , Ping Liu , Bin Dai
{"title":"I2 促进的吡咯并[1,2-a]喹喔啉的直接 C-H 芳基硒化反应","authors":"Di Hao , Zhen Yang , Luigi Vaccaro , Ping Liu , Bin Dai","doi":"10.1016/j.tet.2024.134287","DOIUrl":null,"url":null,"abstract":"<div><div>An I<sub>2</sub>-promoted C–H arylselenylation of pyrrolo[1,2-<em>a</em>]quinoxalines with diaryl diselenides is developed, providing an efficient route to a series of 1 (or 3)-arylselenylated and/or 1,3-diaryl diselenylated pyrrolo[1,2-<em>a</em>]quinoxalines. The methodology is characterised by a wide range of substrates, good functional group tolerance and gram-level synthesis. Further transformations of the products to form structurally diverse pyrrolo[1,2-<em>a</em>]quinoxalines were successfully achieved. Similarly, I<sub>2</sub>-promoted C–H sulfenylation of pyrrolo[1,2-<em>a</em>]quinoxaline with 1,2-diphenyldisulfane were investigated. We believe that these novel pyrrolo[1,2-<em>a</em>]quinoxaline compounds will have promising applications in pharmaceutical synthesis.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"167 ","pages":"Article 134287"},"PeriodicalIF":2.1000,"publicationDate":"2024-09-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"I2-promoted direct C–H arylselenylation of pyrrolo[1,2-a]quinoxalines\",\"authors\":\"Di Hao , Zhen Yang , Luigi Vaccaro , Ping Liu , Bin Dai\",\"doi\":\"10.1016/j.tet.2024.134287\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>An I<sub>2</sub>-promoted C–H arylselenylation of pyrrolo[1,2-<em>a</em>]quinoxalines with diaryl diselenides is developed, providing an efficient route to a series of 1 (or 3)-arylselenylated and/or 1,3-diaryl diselenylated pyrrolo[1,2-<em>a</em>]quinoxalines. The methodology is characterised by a wide range of substrates, good functional group tolerance and gram-level synthesis. Further transformations of the products to form structurally diverse pyrrolo[1,2-<em>a</em>]quinoxalines were successfully achieved. Similarly, I<sub>2</sub>-promoted C–H sulfenylation of pyrrolo[1,2-<em>a</em>]quinoxaline with 1,2-diphenyldisulfane were investigated. We believe that these novel pyrrolo[1,2-<em>a</em>]quinoxaline compounds will have promising applications in pharmaceutical synthesis.</div></div>\",\"PeriodicalId\":437,\"journal\":{\"name\":\"Tetrahedron\",\"volume\":\"167 \",\"pages\":\"Article 134287\"},\"PeriodicalIF\":2.1000,\"publicationDate\":\"2024-09-30\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Tetrahedron\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S004040202400468X\",\"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":"Tetrahedron","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S004040202400468X","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
I2-promoted direct C–H arylselenylation of pyrrolo[1,2-a]quinoxalines
An I2-promoted C–H arylselenylation of pyrrolo[1,2-a]quinoxalines with diaryl diselenides is developed, providing an efficient route to a series of 1 (or 3)-arylselenylated and/or 1,3-diaryl diselenylated pyrrolo[1,2-a]quinoxalines. The methodology is characterised by a wide range of substrates, good functional group tolerance and gram-level synthesis. Further transformations of the products to form structurally diverse pyrrolo[1,2-a]quinoxalines were successfully achieved. Similarly, I2-promoted C–H sulfenylation of pyrrolo[1,2-a]quinoxaline with 1,2-diphenyldisulfane were investigated. We believe that these novel pyrrolo[1,2-a]quinoxaline compounds will have promising applications in pharmaceutical synthesis.
期刊介绍:
Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry.
Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters.
Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.