4.8 Article

Synthesis of 1,2,4-Triazol-3-imines via Selective Stepwise Cycloaddition of Nitrile Imines with Organo-cyanamides

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ORGANIC LETTERS
卷 20, 期 14, 页码 4263-4266

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AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b01673

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  1. EPSRC [EP/N00969X/1]
  2. University of Lincoln
  3. ARC [FT170100156]

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A convenient method for the synthesis of 1,2,4-triazol-3-imines through a selective, formal, 1,3-dipolar cycloaddition of organo-cyanamide ions with nitrile imine dipoles is reported. Hydrolysis of the 1,2,4-triazol-3-imines yields the corresponding 1,2,4-triazol-5-ones. A stepwise mechanism, supported by DFT calculations, is invoked to explain the reaction selectivity.

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