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DBU促进的2-氨基-4-色原酮与β-硝基苯乙烯和/或芳醛的串联选择性亲核加成/C-C键裂解/杂环狄尔斯-阿尔德反应:通向5-色烯并[2,3-]吡啶-5-酮的方法。

DBU-Promoted Cascade Selective Nucleophilic Addition/C-C Bond Cleavage/Hetero-Diels-Alder Reactions of 2-Amino-4-chromen-4-ones with β-Nitrostyrenes and/or Aryl Aldehydes: Access to 5-Chromeno[2,3-]pyridin-5-ones.

作者信息

Luo Naili, Wang Shan, Zhang Yue, Xin Junhu, Wang Cunde

机构信息

School of Chemistry and Chemical Engineering, Yangzhou University,180 Siwangting Street, Yangzhou 225002, P. R. China.

出版信息

J Org Chem. 2020 Nov 6;85(21):14219-14228. doi: 10.1021/acs.joc.0c01993. Epub 2020 Oct 29.

Abstract

DBU-promoted cascade selective nucleophilic addition/C-C bond cleavage/hetero-Diels-Alder reactions accompanied by aromatization of substituted 2-amino-4-chromen-4-ones with substituted β-nitrostyrenes or with the combined substituted β-nitrostyrenes and aromatic aldehydes were developed for the synthesis of 2,4-diaryl-substituted 5-chromeno[2,3-]pyridin-5-ones. This procedure provides a highly efficient and facile route to functionalized 5-chromeno[2,3-]pyridines from readily available substrates under mild reaction conditions.

摘要

开发了DBU促进的级联选择性亲核加成/C-C键裂解/杂环狄尔斯-阿尔德反应,该反应伴随着取代的2-氨基-4-色烯-4-酮与取代的β-硝基苯乙烯或与取代的β-硝基苯乙烯和芳香醛的组合进行芳构化反应,用于合成2,4-二芳基取代的5-色烯并[2,3-]吡啶-5-酮。该方法为在温和反应条件下从易得的底物合成功能化的5-色烯并[2,3-]吡啶提供了一条高效且简便的途径。

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