Copper-catalyzed intramolecular cyclization of N-propargyl-adenine: synthesis of purine-fused tricyclics

J Org Chem. 2014 Apr 18;79(8):3665-70. doi: 10.1021/jo5001687. Epub 2014 Apr 4.

Abstract

A novel protocol to construct fluorescent purine-fused tricyclic products via intramolecular cyclization of N-propargyl-adenine has been developed. With CuBr as the catalyst, a series of purine-fused tricyclic products were obtained in good to excellent yields (19 examples, 75-89% yields). When R2 was a hydrogen atom in N-propargyl-adenines, the reactions only afforded the endocyclic double bond products. When R2 was an aryl group, the electron-donating groups favored the endocyclic double bond products, while the electron-withdrawing groups favored the exocyclic double bond products.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenine / chemistry*
  • Catalysis
  • Copper / chemistry*
  • Cyclization
  • Molecular Structure
  • Morphinans / chemistry*
  • Polycyclic Compounds / chemical synthesis*
  • Polycyclic Compounds / chemistry
  • Purines / chemical synthesis*
  • Purines / chemistry

Substances

  • Morphinans
  • N-propargyl
  • Polycyclic Compounds
  • Purines
  • Copper
  • Adenine
  • purine