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

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...

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Published inOrganic letters Vol. 15; no. 3; pp. 642 - 645
Main Authors Tran, Tuan P, Mullins, Patrick B, am Ende, Christopher W, Pettersson, Martin
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.02.2013
Amer Chemical Soc
Subjects
Catalysis
Chemistry
Chemistry, Organic
Combinatorial Chemistry Techniques
Cyclization
Heterocyclic Compounds, 2-Ring - chemical synthesis
Heterocyclic Compounds, 2-Ring - chemistry
Molecular Structure
Physical Sciences
Picolinic Acids - chemistry
Pyrazines - chemical synthesis
Pyrazines - chemistry
Pyridines - chemical synthesis
Pyridines - chemistry
Science & Technology
DRUG
ALIGNMENT
MOLECULAR-PROPERTIES
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Summary: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.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol303463e