9-methyl-4-(methylthio)-2-oxo-2H-pyrano[2',3':4,5]imidazo[1,2-a]pyridine-3-carbonitrile | 1210317-40-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 9-methyl-4-(methylthio)-2-oxo-2H-pyrano[2',3':4,5]imidazo[1,2-a]pyridine-3-carbonitrile
• 英文别名: 10-Methyl-3-methylsulfanyl-5-oxo-6-oxa-1,8-diazatricyclo[7.4.0.02,7]trideca-2(7),3,8,10,12-pentaene-4-carbonitrile；10-methyl-3-methylsulfanyl-5-oxo-6-oxa-1,8-diazatricyclo[7.4.0.02,7]trideca-2(7),3,8,10,12-pentaene-4-carbonitrile
• CAS: 1210317-40-0
• 化学式: C₁₃H₉N₃O₂S
• 分子量: 271.299
• InChiKey: RHIMRLCUTJQNFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  92.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  ethyl 2-cyano-3-(2-hydroxy-8-methylimidazo[1,2-a]pyridin-3-yl)-3-(methylthio)acrylate 150.0 ℃ 、399.97 Pa 条件下， 反应 0.17h， 以50%的产率得到9-methyl-4-(methylthio)-2-oxo-2H-pyrano[2',3':4,5]imidazo[1,2-a]pyridine-3-carbonitrile
  参考文献：
  名称：

  A New Approach to Imidazo[1,2-a]pyridine Derivatives and Their Application to the Syntheses of Novel 2H-Pyrano[2’,3’:4,5]imidazo[1,2-a]pyridin-2-one Derivatives

  摘要：

  3-[Bis(methylthio)methylene]-2(3H)-imidazo[1,2-a]pyridinones were prepared from the S-alkylation of pyridinium 1-[1-carbamoyl-1-[(methylthio) thiocarbonyl]]methylides with methyl iodide followed by the alkaline treatment of the resulting pyridinium salts. The reactions of these 3-methylene-2(3H)-imidazo[1,2-a]pyridinones with some ethyl cyano- or acyl-substituted acetates in the presence of a base did not afford the initially expected 2H-pyrano[2',3':4,5]imidazo[1,2-a]pyridine-2-one derivatives, but, instead of them, provided ethyl 3[2-hydroxyimidazo[1,2-a]pyridin-3-yl]acrylates. The thermolyses of these acrylates without any solvent under reduced pressure gave the corresponding 2H-pyrano[2',3':4,5]imidazo[1,2-a]pyridine-2-one derivatives.

  DOI：

  10.3987/com-09-s(s)41

文献信息

• A New Approach to Imidazo[1,2-a]pyridine Derivatives and Their Application to the Syntheses of Novel 2H-Pyrano[2’,3’:4,5]imidazo[1,2-a]pyridin-2-one Derivatives
  作者：Akikazu Kakehi、Takashi Abe、Yukihisa Okumura、Hiroyuki Suga

  DOI：10.3987/com-09-s(s)41

  日期：——

  3-[Bis(methylthio)methylene]-2(3H)-imidazo[1,2-a]pyridinones were prepared from the S-alkylation of pyridinium 1-[1-carbamoyl-1-[(methylthio) thiocarbonyl]]methylides with methyl iodide followed by the alkaline treatment of the resulting pyridinium salts. The reactions of these 3-methylene-2(3H)-imidazo[1,2-a]pyridinones with some ethyl cyano- or acyl-substituted acetates in the presence of a base did not afford the initially expected 2H-pyrano[2',3':4,5]imidazo[1,2-a]pyridine-2-one derivatives, but, instead of them, provided ethyl 3[2-hydroxyimidazo[1,2-a]pyridin-3-yl]acrylates. The thermolyses of these acrylates without any solvent under reduced pressure gave the corresponding 2H-pyrano[2',3':4,5]imidazo[1,2-a]pyridine-2-one derivatives.