(bis(methylthio))methylidene-8-methylimidazo[1,2-a]pyridin-2(3H)-one | 1210317-16-0

• 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: (bis(methylthio))methylidene-8-methylimidazo[1,2-a]pyridin-2(3H)-one
• 英文别名: 3-[bis(methylthio)methylene]-8-methyl-2(3H)-imidazo[1,2-a]pyridinone；3-[Bis(methylsulfanyl)methylidene]-8-methylimidazo[1,2-a]pyridin-2-one
• CAS: 1210317-16-0
• 化学式: C₁₁H₁₂N₂OS₂
• 分子量: 252.361
• InChiKey: UIEBVUWUWPHKOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  83.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (bis(methylthio))methylidene-8-methylimidazo[1,2-a]pyridin-2(3H)-one 在 potassium tert-butylate 作用下， 以 氯仿 、 叔丁醇 为溶剂， 反应 12.0h， 生成 2',3'-dihydro-8'-methyl-2-methylamino-2',4-dioxospiro[2-cyclopenten-1,3'-imidazo[1,2-a]pyridin]-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis of Spiro[2-cyclopentene-1,3’-imidazo[1,2-a]pyridine] Derivatives and Their Interesting Behavior in 1H-NMR Spectra in Deuteriochloroform

  摘要：

  Ethyl 2',3'-dihydro-2-methylthio-2',4-dioxospiro[2-cyclopentene-1,3'-imidazo[1,2-a]pyridine]-3-carboxylates were synthesized from the reactions of 3-[bis(methylthio)methylene]-2(3H)-imidazo[1,2-a]pyridinones with ethyl 4-chloroacetoacetate in the presence of a base. The 2-methylthio group in these Spiro compounds was easily replaced with some primary and secondary amines to afford the corresponding 2-amino derivatives. Very interestingly, the proton signals of these Spiro compounds in the H-1-NMR spectra in deuteriochloroform (CDCl3) changed with an increase in the sample concentration, and the analysis for the magnitude and the direction of each proton shift disclosed the conformational change of the cyclopentenone moiety in this molecule.

  DOI：

  10.3987/com-10-11985
• 作为产物：
  描述：

  2-(3-Methylpyridin-1-ium-1-yl)-3,3-bis(methylsulfanyl)prop-2-enamide;iodide 在 potassium tert-butylate 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 (bis(methylthio))methylidene-8-methylimidazo[1,2-a]pyridin-2(3H)-one
  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

• CN115368357
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.
• Synthesis of Spiro[2-cyclopentene-1,3’-imidazo[1,2-a]pyridine] Derivatives and Their Interesting Behavior in 1H-NMR Spectra in Deuteriochloroform
  作者：Akikazu Kakehi、Takashi Abe、Hiroyuki Suga、Yukihisa Okumura、Kennosuke Itoh

  DOI：10.3987/com-10-11985

  日期：——

  Ethyl 2',3'-dihydro-2-methylthio-2',4-dioxospiro[2-cyclopentene-1,3'-imidazo[1,2-a]pyridine]-3-carboxylates were synthesized from the reactions of 3-[bis(methylthio)methylene]-2(3H)-imidazo[1,2-a]pyridinones with ethyl 4-chloroacetoacetate in the presence of a base. The 2-methylthio group in these Spiro compounds was easily replaced with some primary and secondary amines to afford the corresponding 2-amino derivatives. Very interestingly, the proton signals of these Spiro compounds in the H-1-NMR spectra in deuteriochloroform (CDCl3) changed with an increase in the sample concentration, and the analysis for the magnitude and the direction of each proton shift disclosed the conformational change of the cyclopentenone moiety in this molecule.