Anticoccidials. VII. Synthesis of 4,5-dihydro-5-oxo-2-pyrazinecarboxylic acid 1-oxides.

Abstract
Hydrolysis of 1,6-dihydro-6-oxo-2,3-pyrazinedicarbonitrile (4) gave sodium hydrogen 1,6-dihydro-6-oxo-2,3pyrazinedicarboxylate (6), which was converted to methyl 1,6dihydro-6-oxo-2-pyrazinecarboxylate (10) and methyl 4,5-dihydro-5-oxo-2-pyrazinecarboxylate (12) via a sequence of reactions including decarboxylation and esterification. Although the synthesis of 4,5-dihydro-5-oxo-2-pyrazinecarboxylic acid 1-oxide (2) from 12 was unsuccessful, its 6-methyl derivative 3 was synthesized from the 5-methyl analog of 4.

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