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

Yan Ming Chen, Kwunmin Chen

Research output: Contribution to journalArticle

Abstract

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
Volume62
Issue number10
DOIs
Publication statusPublished - 2015 Oct 1

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Amination
Stereoselectivity
Cyclization
Aldehydes
Derivatives
diphenylprolinol trimethylsilyl ether
1,3-indandione

Keywords

  • Cascade reaction
  • Hexahydropyridazine
  • Michael reaction
  • Organocatalyst

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "Three-Component Triple Organocascade Synthesis of Hexahydropyridazine Derivatives via a Sequential Michael/Amination/Cyclization Reaction",
abstract = "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.).",
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N2 - 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.).

AB - 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.).

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