Synthesis of pyridopyrazine-1,6-diones from 6-hydroxypicolinic acids via a one-pot coupling/cyclization reaction

Org Lett. 2013 Feb 1;15(3):642-5. doi: 10.1021/ol303463e. Epub 2013 Jan 18.

Abstract

A facile one-pot synthesis of 3,4-dihydro-1H-pyrido[1,2-a]pyrazine-1,6(2H)-diones (pyridopyrazine-1,6-diones) has been developed which employs a sequential coupling/cyclization reaction of 6-hydroxypicolinic acids and β-hydroxylamines. The transformation proceeds in good yield under mild conditions using O-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU) to both carry out the amide formation and activate the hydroxyl group for intramolecular alkylation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Combinatorial Chemistry Techniques
  • Cyclization
  • Heterocyclic Compounds, 2-Ring / chemical synthesis*
  • Heterocyclic Compounds, 2-Ring / chemistry
  • Molecular Structure
  • Picolinic Acids / chemistry*
  • Pyrazines / chemical synthesis*
  • Pyrazines / chemistry
  • Pyridines / chemical synthesis*
  • Pyridines / chemistry

Substances

  • 6-hydroxypicolinic acid
  • Heterocyclic Compounds, 2-Ring
  • Picolinic Acids
  • Pyrazines
  • Pyridines