4.7 Article

Bicyclization of Isocyanides with Alkenoyl Bis(ketene dithioacetals): Access to 6,7-Dihydro-1H-indol-4(5H)-ones

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 12, Pages 5929-5933

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo500928c

Keywords

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Funding

  1. NNSFC [21172030, 21272034, 21202015]
  2. Young Scientific Research Foundation of Jilin Province [20140520083JH]
  3. Fundamental Research Funds for the Central Universities [12QNJJ010]

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The tandem [3 + 2] cycloaddition/intramolecular imidoyl anion trapping strategy has been successfully applied for the synthesis of 6,7-dihydro-1H-indol-4(5H)-ones from alkenoyl bis(ketene dithioacetals) and tosylmethyl isocyanide. The reaction proceeded smoothly under mild reaction conditions to afford bicyclization products in high to excellent yields in a single step.

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