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

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• 作者：Tuan P. Tran ; Patrick B. Mullins ; Christopher W. am Ende ; Martin Pettersson
• 刊名：Organic Letters
• 出版年：2013
• 出版时间：February 1, 2013
• 年：2013
• 卷：15
• 期：3
• 页码：642-645
• 全文大小：269K
• 年卷期：v.15,no.3(February 1, 2013)
• ISSN：1523-7052

文摘

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 尾-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.