{"title":"Expeditious synthesis of CF<sub>3</sub>-phenanthridones through a base-mediated cross-conjugated vinylogous benzannulation (VBA).","authors":"Madhu Desagoni, Chavakula Nagababu, Nagender Punna","doi":"10.1039/d4ob01480d","DOIUrl":null,"url":null,"abstract":"<p><p>Herein, we report a mild, efficient, and rapid approach for the preparation of CF<sub>3</sub>-phenanthridones through a cross-conjugated vinylogous [4 + 2] benzannulation of easily accessible 4-methyl-3-trifluoroacetylquinolones and nitro-olefins. The present transformation is superior to previous approaches for obtaining CF<sub>3</sub>-phenanthridones, in that it proceeds exclusively with the assistance of a simple base, eliminating the need for transition metal catalysts or oxidants. The strong electron-withdrawing nature of the CF<sub>3</sub>-group present in the quinolone moiety promotes the formation of a reactive cross-conjugated vinylogous enolate.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9000,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d4ob01480d","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
Herein, we report a mild, efficient, and rapid approach for the preparation of CF3-phenanthridones through a cross-conjugated vinylogous [4 + 2] benzannulation of easily accessible 4-methyl-3-trifluoroacetylquinolones and nitro-olefins. The present transformation is superior to previous approaches for obtaining CF3-phenanthridones, in that it proceeds exclusively with the assistance of a simple base, eliminating the need for transition metal catalysts or oxidants. The strong electron-withdrawing nature of the CF3-group present in the quinolone moiety promotes the formation of a reactive cross-conjugated vinylogous enolate.
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