Copper-Catalyzed Reactions of Alkenyl Boronic Esters via Chan-Evans-Lam Coupling/Annulation Cascades: Substrate Selective Synthesis of Dihydroquinazolin-4-ones and Polysubstituted Quinolines
Copper-Catalyzed Reactions of Alkenyl Boronic Esters via Chan-Evans-Lam Coupling/Annulation Cascades: Substrate Selective Synthesis of Dihydroquinazolin-4-ones and Polysubstituted Quinolines
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DOI：
10.1021/acs.orglett.2c02522
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发表时间：
2022-08-29
期刊：
影响因子：
5.2
通讯作者：
Wei, Yu
中科院分区：
文献类型：
--
作者：
Li, Yuge;Cao, Zifeng;Wei, Yu
建立了铜催化的烯基硼酸酯与N-H类亲核试剂的级联环化反应，为一锅法组装氮杂环化合物提供了新的途径。在Chan-Evans-Lam C-N偶联之后，环化过程基于所利用的底物经由不同途径发生，从而提供氢胺化产物二氢喹唑啉-4-酮或芳构化产物喹啉。通过这种一锅C-N偶联/成环级联，在每种情况下都可以以中等至良好的产率获得目标取代的氮杂环。
Copper-catalyzed cascade cyclization reactions between alkenyl boronic esters and N-H-based nucleophiles have been established, providing new approaches for one-pot assembly of azacycles. Following the Chan-Evans-Lam C-N couplings, the cyclization processes occur via divergent pathways based on the utilized substrates, affording hydroamination product dihydroquinazolin-4-ones or aromatization product quinolines. Via this one-pot C-N coupling/annulation cascade, the target substituted azacycles can be obtained in moderate to good yields in each case.