{"title":"n -杂环碳催化[4 + 2]环化可烯化硫酯合成2-吡咯酮","authors":"Jinfeng Zhang, Chen Zhu, Xu Cao, Hui Jin* and Lixin Zhang*, ","doi":"10.1021/acs.joc.5c0042810.1021/acs.joc.5c00428","DOIUrl":null,"url":null,"abstract":"<p >An <i>N</i>-heterocyclic carbene (NHC)-catalyzed [4 + 2] annulation enables the direct synthesis of 2-pyrones from α-chlorothioesters and β,γ-unsaturated α-keto esters or chalcones. The method utilizes NHC-activated α-chlorothioesters to generate key intermediates for 2-pyrone formation with high functional group tolerance. Moreover, the 2-pyrones were transformed into polysubstituted benzene and naphthalene derivatives, showcasing their synthetic value.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 17","pages":"6094–6101 6094–6101"},"PeriodicalIF":3.3000,"publicationDate":"2025-04-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"N-Heterocyclic Carbene-Catalyzed [4 + 2] Annulation of Enolizable Thioesters for the Synthesis of 2-Pyrones\",\"authors\":\"Jinfeng Zhang, Chen Zhu, Xu Cao, Hui Jin* and Lixin Zhang*, \",\"doi\":\"10.1021/acs.joc.5c0042810.1021/acs.joc.5c00428\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >An <i>N</i>-heterocyclic carbene (NHC)-catalyzed [4 + 2] annulation enables the direct synthesis of 2-pyrones from α-chlorothioesters and β,γ-unsaturated α-keto esters or chalcones. The method utilizes NHC-activated α-chlorothioesters to generate key intermediates for 2-pyrone formation with high functional group tolerance. Moreover, the 2-pyrones were transformed into polysubstituted benzene and naphthalene derivatives, showcasing their synthetic value.</p>\",\"PeriodicalId\":57,\"journal\":{\"name\":\"Journal of Organic Chemistry\",\"volume\":\"90 17\",\"pages\":\"6094–6101 6094–6101\"},\"PeriodicalIF\":3.3000,\"publicationDate\":\"2025-04-23\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Organic Chemistry\",\"FirstCategoryId\":\"1\",\"ListUrlMain\":\"https://pubs.acs.org/doi/10.1021/acs.joc.5c00428\",\"RegionNum\":2,\"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":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.joc.5c00428","RegionNum":2,"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
摘要
n -杂环羰基(NHC)催化的[4 + 2]环化使α-氯硫酯和β,γ-不饱和α-酮酯或查尔酮直接合成2-吡咯酮。该方法利用nhc活化的α-氯硫酯生成具有高官能团耐受性的2-吡啶酮生成关键中间体。并将2-吡咯酮转化为多取代苯和萘衍生物,显示了它们的合成价值。
N-Heterocyclic Carbene-Catalyzed [4 + 2] Annulation of Enolizable Thioesters for the Synthesis of 2-Pyrones
An N-heterocyclic carbene (NHC)-catalyzed [4 + 2] annulation enables the direct synthesis of 2-pyrones from α-chlorothioesters and β,γ-unsaturated α-keto esters or chalcones. The method utilizes NHC-activated α-chlorothioesters to generate key intermediates for 2-pyrone formation with high functional group tolerance. Moreover, the 2-pyrones were transformed into polysubstituted benzene and naphthalene derivatives, showcasing their synthetic value.
期刊介绍:
Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.