title: Synthesis of pyridopyrazine-1,6-diones from 6-hydroxypicolinic acids via a one-pot coupling/cyclization reaction.
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.
authors: Neuroscience Medicinal Chemistry, Pfizer Worldwide Research and Development, Eastern Point Road, Groton, Connecticut 06340, USA. tuan.tran@pfizer.com
authors: Tuan P
authors: TP
authors: Tran
authors: Patrick B
authors: PB
authors: Mullins
authors: Christopher W
authors: CW
authors: am Ende
authors: Martin
authors: M
authors: Pettersson
mesh_terms: D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010848:Picolinic Acids / Q000737:chemistry*; D011719:Pyrazines / Q000138:chemical synthesis* / Q000737:chemistry; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C477454:6-hydroxypicolinic acid; D006574:Heterocyclic Compounds, 2-Ring; D010848:Picolinic Acids; D011719:Pyrazines; D011725:Pyridines