{"title":"银催化的吡喃杂环的区域选择性合成:获得翅果喹啉 A 衍生物的多功能途径。","authors":"Kapil Chahal, Ravikumar Badhavath, Simran Kaur Matharu, Anjana Vinod, Damera Vani, Vijaya Rani Potluri, Balasubramanian Sridhar, Kallu Rajender Reddy","doi":"10.1039/d4ob01446d","DOIUrl":null,"url":null,"abstract":"<p><p>This study introduces a silver-catalyzed method for the efficient and regioselective synthesis of pyrano heterocycles, utilizing readily available alcohols and water as nucleophiles. The method demonstrates high efficiency, delivering excellent yields and selectivity, and is scalable to gram quantities while maintaining broad functional group tolerance. Notably, the synthesized pyrano[3,4-<i>c</i>]quinolines were successfully transformed into diverse samoquasine A derivatives, underscoring the method's applicability in natural product synthesis. This work represents a significant advancement in pyrano heterocycle synthesis, offering a practical route to valuable compounds with potential applications in pharmaceutical and chemical research.</p>","PeriodicalId":2,"journal":{"name":"ACS Applied Bio Materials","volume":null,"pages":null},"PeriodicalIF":4.6000,"publicationDate":"2024-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Silver-catalyzed regioselective synthesis of pyrano heterocycles: a versatile route to samoquasine A derivatives.\",\"authors\":\"Kapil Chahal, Ravikumar Badhavath, Simran Kaur Matharu, Anjana Vinod, Damera Vani, Vijaya Rani Potluri, Balasubramanian Sridhar, Kallu Rajender Reddy\",\"doi\":\"10.1039/d4ob01446d\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>This study introduces a silver-catalyzed method for the efficient and regioselective synthesis of pyrano heterocycles, utilizing readily available alcohols and water as nucleophiles. The method demonstrates high efficiency, delivering excellent yields and selectivity, and is scalable to gram quantities while maintaining broad functional group tolerance. Notably, the synthesized pyrano[3,4-<i>c</i>]quinolines were successfully transformed into diverse samoquasine A derivatives, underscoring the method's applicability in natural product synthesis. This work represents a significant advancement in pyrano heterocycle synthesis, offering a practical route to valuable compounds with potential applications in pharmaceutical and chemical research.</p>\",\"PeriodicalId\":2,\"journal\":{\"name\":\"ACS Applied Bio Materials\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":4.6000,\"publicationDate\":\"2024-10-15\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"ACS Applied Bio Materials\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1039/d4ob01446d\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"MATERIALS SCIENCE, BIOMATERIALS\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"ACS Applied Bio Materials","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d4ob01446d","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"MATERIALS SCIENCE, BIOMATERIALS","Score":null,"Total":0}
引用次数: 0
摘要
本研究介绍了一种银催化方法,利用现成的醇和水作为亲核剂,高效、区域选择性地合成吡喃杂环。该方法效率高,产率和选择性极佳,在保持广泛的官能团耐受性的同时,可扩展到克级数量。值得注意的是,合成的吡喃并[3,4-c]喹啉成功地转化成了多种翅果喹啉 A 衍生物,强调了该方法在天然产物合成中的适用性。这项工作代表了吡喃杂环合成领域的重大进展,提供了一条获得有价值化合物的实用途径,有望应用于制药和化学研究领域。
Silver-catalyzed regioselective synthesis of pyrano heterocycles: a versatile route to samoquasine A derivatives.
This study introduces a silver-catalyzed method for the efficient and regioselective synthesis of pyrano heterocycles, utilizing readily available alcohols and water as nucleophiles. The method demonstrates high efficiency, delivering excellent yields and selectivity, and is scalable to gram quantities while maintaining broad functional group tolerance. Notably, the synthesized pyrano[3,4-c]quinolines were successfully transformed into diverse samoquasine A derivatives, underscoring the method's applicability in natural product synthesis. This work represents a significant advancement in pyrano heterocycle synthesis, offering a practical route to valuable compounds with potential applications in pharmaceutical and chemical research.