4.8 Article

Cu(II)/lodine(III) Oxide Dimerization of Heterocyclic Ketene Aminals: Tandem TEMPO Oxidation for the Highly Selective Synthesis of Functionalized 2H-Pyrrolo[1,2-a]imidazol-7(3H)-ones

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ORGANIC LETTERS
卷 22, 期 21, 页码 8210-8214

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AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c02689

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资金

  1. NSFC [21662042]
  2. Natural Science Foundation of Yunnan Province [2017FA003, 2019FY003003]
  3. Ministry of Education of the People's Republic of China [IRT17R94]
  4. Innovation Team of Yunnan Education Department
  5. Project of Yunnan Education Department [2019J0012]

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This study aimed to develop a novel protocol for the synthesis of 2H-pyrrolo[1,2-a]imidazol-7(3H)-ones (PIDOs) from heterocyclic ketene aminals (HKAs) through an unprecedented cascade reaction by refluxing. Consequently, a series of PIDOs was produced through an amazing oxidative dimerization, followed by sequential cleavage of the C-N and C-C bonds in dimeric HKAs. This formation of PIDOs was accompanied by the formation and cleavage of many bonds. This method is suitable for the parallel construction of bicyclic pyrrolidone-like products.

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