Yuanmu Zhang , Lingxuan Zhu , Yi Lu , Xinsheng Lei , Yingxia Li
{"title":"“One pot” synthesis of quinazolinone-[2,3]-fused polycyclic scaffolds in a three-step reaction sequence†","authors":"Yuanmu Zhang , Lingxuan Zhu , Yi Lu , Xinsheng Lei , Yingxia Li","doi":"10.1039/d4ob00529e","DOIUrl":null,"url":null,"abstract":"<div><p>Diverse quinazolinone-[2,3]-fused polycyclic skeletons occupy a prominent position in drug discovery. Even with currently available methods there still remain unmet needs for flexible access to such structures. Herein, we have explored a mild “one pot” procedure for the construction of various quinazolinone-[2,3]-fused polycycles. The procedure involves Pd-catalyzed carbonylation of <em>N</em>-(2-iodophenyl)acetamides, release of the masked terminal amine, and two sequential and spontaneous cyclizations. This generally applicable approach features easy assembly of precursors from readily available starting materials, mild reaction conditions, non-cumbersome operation, and polycyclic diversity.</p></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9000,"publicationDate":"2024-06-12","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/S1477052024004671","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Diverse quinazolinone-[2,3]-fused polycyclic skeletons occupy a prominent position in drug discovery. Even with currently available methods there still remain unmet needs for flexible access to such structures. Herein, we have explored a mild “one pot” procedure for the construction of various quinazolinone-[2,3]-fused polycycles. The procedure involves Pd-catalyzed carbonylation of N-(2-iodophenyl)acetamides, release of the masked terminal amine, and two sequential and spontaneous cyclizations. This generally applicable approach features easy assembly of precursors from readily available starting materials, mild reaction conditions, non-cumbersome operation, and polycyclic diversity.