Straightforward and highly efficient catalyst-free one-step synthesis of 2-(purin-6-yl)acetoacetic acid ethyl esters, (purin-6-yl)acetates, and 6-methylpurines through S(N)Ar-based reactions of 6-halopurines with ethyl acetoacetate

Org Lett. 2009 Apr 16;11(8):1745-8. doi: 10.1021/ol9002256.

Abstract

A novel approach to the synthesis of purines bearing functionalized carbon substituents or methyl in position 6 was developed. Under different reaction conditions, 6-halopurine derivatives could react with ethyl acetoacetate efficiently to yield 2-(purin-6-yl)acetoacetic acid ethyl esters, (purin-6-yl)acetates and 6-methylpurines respectively. No metal catalyst and ligand were required.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetoacetates / chemistry*
  • Combinatorial Chemistry Techniques
  • Esters
  • Hydrocarbons, Halogenated / chemistry*
  • Molecular Structure
  • Purines / chemical synthesis*
  • Purines / chemistry*

Substances

  • Acetoacetates
  • Esters
  • Hydrocarbons, Halogenated
  • Purines
  • ethyl acetoacetate