Copper Catalysis for Nicotinate Synthesis through beta-Alkenylation/Cyclization of Saturated Ketones with beta-Enamino Esters

Copper Catalysis for Nicotinate Synthesis through beta-Alkenylation/Cyclization of Saturated Ketones with beta-Enamino Esters
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铜催化饱和酮与 β-烯氨基酯的 β-烯基化/环化合成烟酸酯

DOI:
10.1002/adsc.201701031
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发表时间:
2018
影响因子:
5.4
通讯作者:
Zhong Weihui
Zhong Weihui
中科院分区:
化学2区
文献类型:
--
作者:
Ling Fei;Xiao Lian;Fang Lu;Lv Yaping;Zhong Weihui

文献摘要

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本文报道了第一个铜催化的4-OH-TEMPO催化的饱和酮与β-烯氨基酸酯的分子间[3+3]环化反应,并成功地通过β-C(Sp3)-H键烯基化、烯胺-羰基缩合和芳构化反应合成了多种烟酸酯。该方案可以容忍多种官能团,从而为制备5H-色烯并[4,3-b]吡啶-5-酮骨架提供了一种实用而有效的方法。
The first example of a Cu‐catalyzed and 4‐OH‐TEMPO mediated intermolecular [3+3] annulation of saturated ketones withβ‐enamino esters is reported herein, which was successfully used for the synthesis of versatile nicotinates through sequentialβ‐C(sp3)‐H bond alkenylation, enamine‐carbonyl condensation and aromatization. This protocol tolerates a variety of functional groups, thereby providing a practical and efficient method for the fabrication of5H‐chromeno[4,3‐b]pyridin‐5‐one skeletons.