An unusual Michael addition of 3,3-dimethoxypropanenitrile to 2-aryl acrylates: a convenient route to 4-unsubstituted 5,6-dihydropyrido[2,3-d]pyrimidines

J Org Chem. 2010 Jan 15;75(2):487-90. doi: 10.1021/jo902345r.

Abstract

An unusual Michael addition between 2-aryl-substituted acrylates and 3,3-dimethoxypropanenitrile which leads, depending on the reaction temperature (60 or -78 degrees C, respectively), to a 4-methoxymethylene-substituted 4-cyanobutyric ester or to a 4-dimethoxymethyl 4-cyanobutyric ester is described. These compounds can be subsequently converted to 4-unsubstituted pyrido[2,3-d]pyrimidines upon treatment with a guanidine system under microwave irradiation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acrylates / chemistry*
  • CDC2 Protein Kinase / agonists
  • CDC2 Protein Kinase / chemistry*
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / pharmacology
  • Esters
  • Microwaves
  • Models, Chemical
  • Molecular Structure
  • Neurodegenerative Diseases / drug therapy
  • Nitriles / chemistry*
  • Pyrimidines / chemical synthesis
  • Pyrimidines / chemistry*
  • Structure-Activity Relationship
  • Temperature

Substances

  • 3,3-dimethoxypropanenitrile
  • 5,6-dihydropyrido(2,3-d)pyrimidine
  • Acrylates
  • Enzyme Inhibitors
  • Esters
  • Nitriles
  • Pyrimidines
  • CDC2 Protein Kinase