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

Organic & biomolecular chemistry (2010-04-24)
Krishnananda Samanta, Gautam Panda
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
1-Fluoro-2-nitrobenzene, 99%