Three-Component Triple Organocascade Synthesis of Hexahydropyridazine Derivatives via a Sequential Michael/Amination/Cyclization Reaction

Yan Ming Chen, Kwunmin Chen

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The organocatalytic asymmetric synthesis of hexahydropyridazines were performed through a unique Michael/amination/cyclization reaction. The organocascade reaction proceeded smoothly between 2-arylidene-1,3-indandiones and aldehydes followed by the addition of azodicarboxylates catalyzed by the privileged organocatalyst α,-α-L-diphenylprolinol trimethylsilyl ether (10 mol%) in the presence of a base additive Et3N (20 mo%) at 0 C. A series of substituted hexahydropyridazines were obtained in good to high chemical yields (55-78 %) and reasonable to high levels of stereoselectivities (51-93 % ee and 4 : 1 d.r.).

Original languageEnglish
Pages (from-to)843-849
Number of pages7
JournalJournal of the Chinese Chemical Society
Issue number10
Publication statusPublished - 2015 Oct 1



  • Cascade reaction
  • Hexahydropyridazine
  • Michael reaction
  • Organocatalyst

ASJC Scopus subject areas

  • Chemistry(all)

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