Lithium perchlorate-, acetic anhydride-, and triphenylphosphine-assisted multicomponent syntheses of 4-unsubstituted 2,5-dioxooctahydroquinoline-3- carboxylates and 3-carbonitriles

Xingxian Gu, Gunda I. Georg

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

Lithium perchlorate and acetic anhydride were the key additives for the multi-component reaction between 3-aminocyclohex-2-enones, formaldehyde, and malonates yielding adducts that were annulated under acidic conditions to afford bicyclic 2,5-dioxooctahydroquinoline-3-carboxylates. When methyl cyanoacetate was subjected to the same reaction conditions in the presence of a catalytic amount of triphenylphosphine, the bicyclic 2,5-dioxooctahydroquinoline-3- carbonitriles were obtained in a one-flask reaction.

Original languageEnglish (US)
Pages (from-to)9406-9416
Number of pages11
JournalTetrahedron
Volume69
Issue number45
DOIs
StatePublished - Nov 11 2013

Bibliographical note

Funding Information:
We gratefully acknowledge financial support from the NIH ( Grant No. P41 GM076302 and P41 GM081267 ) and the University of Minnesota through the Vince and McKnight Endowed Chairs (to G.I.G).

Keywords

  • 2,5-Dioxooctahydroquinolines
  • Acetic anhydride
  • Catalysis
  • Lithium perchlorate
  • Multicomponent reaction
  • Triphenylphosphine

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