2-(1-phenylethyl)-3,4-dihydro-1H-pyrido[1,2-a]pyrazine-1,6(2H)-dione | 1420476-96-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(1-phenylethyl)-3,4-dihydro-1H-pyrido[1,2-a]pyrazine-1,6(2H)-dione
• 英文别名: 2-(1-phenylethyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,6-dione
• CAS: 1420476-96-5
• 化学式: C₁₆H₁₆N₂O₂
• 分子量: 268.315
• InChiKey: YYJZDSPGDXPWED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.07
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  42.31
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2-[(1-苯基乙基)氨基]乙醇 、 6-羟基吡啶-2-羧酸 在 caesium carbonate 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 乙腈 为溶剂， 以47%的产率得到2-(1-phenylethyl)-3,4-dihydro-1H-pyrido[1,2-a]pyrazine-1,6(2H)-dione
  参考文献：
  名称：

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

  摘要：

  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 beta-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.

  DOI：

  10.1021/ol303463e

文献信息

• Protocol for the Direct Conversion of Lactones to Lactams Mediated by 1,5,7-Triazabicyclo[4.4.0]dec-5-ene: Synthesis of Pyridopyrazine-1,6-diones
  作者：Danica A. Rankic、Cory M. Stiff、Christopher W. am Ende、John M. Humphrey

  DOI：10.1021/acs.joc.7b02079

  日期：2017.12.1

  We present an operationally simple lactone-to-lactam transformation utilizing diverse amine nucleophiles. The key steps of amidation, alcohol activation, and cyclization are all mediated by one reagent (TBD) in a single vessel at room temperature. We illustrate the convenience of this protocol by synthesizing a wide range of N-alkyl, N-aryl, and N-hetereoaryl pyridopyrazine-1,6-diones, an important class of medicinally significant lactams. Furthermore, the reported methodology can be applied to the synthesis of milligram to hundred gram quantities of pyridopyrazine-1,6-diones without the use of specialized equipment.