American Chemical Society
ol303463e_si_003.cif (11.02 kB)

Synthesis of Pyridopyrazine-1,6-diones from 6‑Hydroxypicolinic Acids via a One-Pot Coupling/Cyclization Reaction

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posted on 2013-02-01, 00:00 authored by Tuan P. Tran, Patrick B. Mullins, Christopher W. am Ende, Martin Pettersson
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.