A new synthesis of amino acid-based enantiomerically pure substituted 2,3,4,4a,5,6-hexahydro-1H-pyrazino[1,2-a]quinoxalines

Org Biomol Chem. 2010 Jun 21;8(12):2823-8. doi: 10.1039/c000029a. Epub 2010 Apr 22.

Abstract

A new series of enantiomerically pure 2,3,4,4a,5,6-hexahydro-1H-pyrazino[1,2-a]quinoxalines were synthesized for the first time in twelve steps from 1-fluoro-2-nitrobenzene and S-amino acids with 13-20% overall yields. First use of intramolecular Mitsunobu cyclization for 1,2,3,4-tetrahydroquinoxalines followed by PPh(3)/I(2)/imidazole mediated 6-exo-tet cyclization were the key steps.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry*
  • Cyclization
  • Nitrobenzenes / chemistry
  • Quinoxalines / chemical synthesis*
  • Stereoisomerism

Substances

  • Amino Acids
  • Nitrobenzenes
  • Quinoxalines
  • 1-fluoro-2-nitrobenzene