Cobalt-catalyzed intramolecular [2 + 2 + 2] cocyclotrimerization of nitrilediynes: an efficient route to tetra- and pentacyclic pyridine derivatives

Org Lett. 2007 Feb 1;9(3):505-8. doi: 10.1021/ol062988t.

Abstract

[reaction: see text] In this paper, we wish to report the intramolecular [2 + 2 + 2] cocyclotrimerization of nitrilediynes catalyzed by the CoI2(dppe)/Zn system at 80 degrees C in CH3CN. Under these reaction conditions, various highly substituted nitrilediynes having steric conjunction at the alpha and beta positions to a nitrile group and a bulkier substitution at the terminal carbon of alkyne undergo [2 + 2 + 2] cocylotrimerization to afford tetra- and pentacyclic pyridine derivatives in good to excellent yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetonitriles / chemistry
  • Alkynes / chemistry*
  • Carbon / chemistry
  • Catalysis
  • Cobalt / chemistry*
  • Cyclization
  • Iodides / chemistry
  • Models, Chemical
  • Nitriles / chemistry*
  • Polymers / chemistry*
  • Pyridines / chemistry*
  • Temperature
  • Zinc / chemistry

Substances

  • Acetonitriles
  • Alkynes
  • Iodides
  • Nitriles
  • Polymers
  • Pyridines
  • Cobalt
  • Carbon
  • Zinc