ethyl 5-amino-2-(o-tolyl)thiazole-4-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 5-amino-2-(o-tolyl)thiazole-4-carboxylate
• 英文别名: Ethyl 5-amino-2-(2-methylphenyl)-1,3-thiazole-4-carboxylate；ethyl 5-amino-2-(2-methylphenyl)-1,3-thiazole-4-carboxylate
• 化学式: C₁₃H₁₄N₂O₂S
• 分子量: 262.332
• InChiKey: BJFKQHKCIGGLRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  93.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-甲苯基硫代甲酰胺 在 吡啶 、 乙酰氯 作用下， 以 水 、 甲苯 、 乙腈 为溶剂， 反应 3.58h， 生成 ethyl 5-amino-2-(o-tolyl)thiazole-4-carboxylate
  参考文献：
  名称：

  A Strecker approach to 2-substituted ethyl 5-aminothiazole-4-carboxylates

  摘要：

  A general approach to 2-substituted ethyl 5-aminothiazole-4-carboxylates is reported herein. Both aliphatic and aromatic thioamides undergo 1,2-addition to ethyl glyoxylate to give hemiaminals which, when treated with acetyl chloride, undergo elimination to the corresponding imines. Upon exposure to aqueous sodium cyanide the imines undergo a Strecker addition-cyclization reaction to provide the target heterocycles in modest to good yields over the 3-step process. (C) 2016 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2015.12.069

文献信息

• A Strecker approach to 2-substituted ethyl 5-aminothiazole-4-carboxylates
  作者：Ken Cheng、Andrew McClory、Whitney Walker、Jie Xu、Haiming Zhang、Remy Angelaud、Francis Gosselin

  DOI：10.1016/j.tetlet.2015.12.069

  日期：2016.4

  A general approach to 2-substituted ethyl 5-aminothiazole-4-carboxylates is reported herein. Both aliphatic and aromatic thioamides undergo 1,2-addition to ethyl glyoxylate to give hemiaminals which, when treated with acetyl chloride, undergo elimination to the corresponding imines. Upon exposure to aqueous sodium cyanide the imines undergo a Strecker addition-cyclization reaction to provide the target heterocycles in modest to good yields over the 3-step process. (C) 2016 Published by Elsevier Ltd.