Preparation of highly substituted 6-arylpurine ribonucleosides by Ni-catalyzed cyclotrimerization. Scope of the reaction

J Org Chem. 2006 Nov 10;71(23):8978-81. doi: 10.1021/jo061485y.

Abstract

Transition metal complex catalyzed cocyclotrimerization of protected alkynylpurine ribonucleosides 1 with various diynes 2 gave rise to a series of 6-arylpurine nucleosides 3 that were further deprotected to free nucleosides 4. Generally, the best yields of cyclotrimerizations were obtained with a catalytic system Ni(cod)2/2PPh(3). On the other hand, CoBr(PPh(3))3 proved to be a superior catalyst for cyclotrimerization of 1 with dipropargyl ether 2g. In addition, Ni catalysis is also suitable for direct cyclotrimerization of unprotected alkynylpurine ribonucleosides 5 to the corresponding 6-arylpurinylribosides 4.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cyclization
  • Molecular Conformation
  • Nickel / chemistry*
  • Purines / chemistry*
  • Ribonucleosides / chemical synthesis*
  • Ribonucleosides / chemistry
  • Stereoisomerism

Substances

  • Purines
  • Ribonucleosides
  • Nickel