3,7,8-trimethylimidazo[1,5-a]quinoxalin-4(5H)-one | 1404093-54-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3,7,8-trimethylimidazo[1,5-a]quinoxalin-4(5H)-one
• 英文别名: 3,7,8-trimethyl-5H-imidazo[1,5-a]quinoxalin-4-one
• CAS: 1404093-54-4
• 化学式: C₁₃H₁₃N₃O
• 分子量: 227.266
• InChiKey: DOIBIUQAYBEFLW-UHFFFAOYSA-N

物化性质

• 沸点：
  347.7±42.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  46.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  tert-butyl (2-amino-4,5-dimethylphenyl)carbamate 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 0.34h， 生成 3,7,8-trimethylimidazo[1,5-a]quinoxalin-4(5H)-one
  参考文献：
  名称：

  A Van Leusen deprotection-cyclization strategy as a fast entry into two imidazoquinoxaline families

  摘要：

  A concise synthesis of two pharmacologically relevant classes of molecules possessing the imidazoquinoxaline core is reported. The protocol involves use of 1,2-phenylenediamines and glyoxylic acid derivatives, namely ethyl glyoxylate or benzylglyoxamide, along with tosylmethylisocyanides in a microwave-assisted Van Leusen three-component condensation. Subsequent unmasking (Boc removal) of an internal amino-nucleophile promotes deprotection and cyclization that take place either spontaneously in a one-pot fashion to give 8 or upon acidic treatment under microwave irradiation after isolation of the imidazole intermediate to give 11. Of note, a tricyclic framework is hence assembled by means of a rapid and straightforward method with a high bond-forming efficiency. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.08.072

文献信息

• A Van Leusen deprotection-cyclization strategy as a fast entry into two imidazoquinoxaline families
  作者：Fabio De Moliner、Christopher Hulme

  DOI：10.1016/j.tetlet.2012.08.072

  日期：2012.10

  A concise synthesis of two pharmacologically relevant classes of molecules possessing the imidazoquinoxaline core is reported. The protocol involves use of 1,2-phenylenediamines and glyoxylic acid derivatives, namely ethyl glyoxylate or benzylglyoxamide, along with tosylmethylisocyanides in a microwave-assisted Van Leusen three-component condensation. Subsequent unmasking (Boc removal) of an internal amino-nucleophile promotes deprotection and cyclization that take place either spontaneously in a one-pot fashion to give 8 or upon acidic treatment under microwave irradiation after isolation of the imidazole intermediate to give 11. Of note, a tricyclic framework is hence assembled by means of a rapid and straightforward method with a high bond-forming efficiency. (C) 2012 Elsevier Ltd. All rights reserved.