Silver triflate and palladium acetate co-catalyzed reaction of N'-(2-alkynylbenzylidene)hydrazide with N-allyl ynamide

Org Lett. 2012 Jun 1;14(11):2790-3. doi: 10.1021/ol301023m. Epub 2012 May 22.

Abstract

A silver triflate and palladium acetate co-catalyzed reaction of N'-(2-alkynylbenzylidene)hydrazide with N-allyl ynamide is described, which generates 2-amino-H-pyrazolo[5,1-a]isoquinolines in good to excellent yield. The transformation proceeds with high efficiency through 6-endo cyclization, [3 + 2] cycloaddition, 3,3-sigmatropic rearrangement, and aromatization.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Amides / chemistry*
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Cyclization
  • Hydrazines / chemistry*
  • Isoquinolines / chemical synthesis*
  • Isoquinolines / chemistry
  • Mesylates / chemistry*
  • Molecular Structure
  • Palladium / chemistry*
  • Silver / chemistry*

Substances

  • Alkynes
  • Amides
  • Hydrazines
  • Isoquinolines
  • Mesylates
  • Silver
  • Palladium
  • trifluoromethanesulfonic acid