Phosphane- and Amine-Catalyzed Ring-Opening Reactions of Cyclopropenones with Isatin Derivatives: Synthesis of Carboxylated 1H-Indoles and Multisubstituted 2H-Pyran-2-ones

Phosphane- and Amine-Catalyzed Ring-Opening Reactions of Cyclopropenones with Isatin Derivatives: Synthesis of Carboxylated 1H-Indoles and Multisubstituted 2H-Pyran-2-ones
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DOI:
10.1002/ejoc.201400077
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发表时间:
2014-05
影响因子:
2.8
通讯作者:
Wenfang Zhao;Xiangying Tang;M. Shi
Wenfang Zhao;Xiangying Tang;M. Shi
中科院分区:
化学3区
文献类型:
--
作者:
Wenfang Zhao;Xiangying Tang;M. Shi

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膦和胺催化的环丙烯酮与靛红衍生物的开环反应给出了不同的反应结果。在膦催化下,以良好的产率提供羧基化的1H-吲哚,并且在胺催化下,以中等产率提供多取代的2 H-吡喃-2-酮。控制实验的基础上,这些反应的机理方面进行了讨论。
The phosphane- and amine-catalyzed ring-opening reactions of cyclopropenones with isatin derivatives give different reaction outcomes. Under phosphane catalysis, carboxylated 1H-indoles are afforded in good yields, and under amine catalysis, multisubstituted 2H-pyran-2-ones are provided in moderate yields. The mechanistic aspects of these reactions are discussed on the basis of control experiments.