4.7 Article

N-Heterocyclic Carbene-Catalyzed Oxidative Annulations of α,β-Unsaturated Aldehydes with Hydrazones: Selective Synthesis of Optically Active 4,5-Dihydropyridazin-3-ones and Pyridazin-3-ones

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 12, Pages 6350-6359

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b00784

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Funding

  1. National Natural Science Foundation of China [21372030]
  2. Program for Changjiang Scholars and Innovative Research Team in University
  3. Beijing Municipal Commission of Education

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A novel and efficient method for the highly enantioselective synthesis of chiral 4,5-dihydropyridazin-3-one derivatives has been developed based on the chiral N-heterocyclic carbene-catalyzed oxidative annulation between alpha,beta-unsaturated aldehydes and hydrazones. Meanwhile, the selective synthesis of either 4,5-dihydropyridazin-3-ones or pyridazin-3-one derivatives from the same reactants has been achieved by simply varying catalytic and reaction conditions.

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