4-(5-methyl-3-nitro-1H-indol-2-yl)thiazole | 1416879-30-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 4-(5-methyl-3-nitro-1H-indol-2-yl)thiazole
• 英文别名: 4-(5-methyl-3-nitro-1H-indol-2-yl)-1,3-thiazole
• CAS: 1416879-30-5
• 化学式: C₁₂H₉N₃O₂S
• 分子量: 259.288
• InChiKey: BHHAKHZFHNYDTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (Z)-2-bromo-4-methyl-N-(2-nitro-1-(thiazol-4-yl)vinyl)aniline 在 四(三苯基膦)钯 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以75%的产率得到4-(5-methyl-3-nitro-1H-indol-2-yl)thiazole
  参考文献：
  名称：

  Microwave-Assisted Synthesis of 3-Nitroindoles from N-Aryl Enamines via Intramolecular Arene–Alkene Coupling

  摘要：

  A variety of N-aryl beta-nitroenamines were effectively transformed into 3-nitroindoles in good yields and with complete regioselectivity via a rapid microwave (mu V) assisted intramolecular arene alkene coupling reaction. This report further demonstrates the versatility of this method by constructing 3-carboalkozy- and 3-cyanoindoles. Optimization data, substrate scope, and applications are discussed.

  DOI：

  10.1021/ol303314x

文献信息

• Microwave-Assisted Synthesis of 3-Nitroindoles from <i>N</i>-Aryl Enamines via Intramolecular Arene–Alkene Coupling
  作者：Huy H. Nguyen、Mark J. Kurth

  DOI：10.1021/ol303314x

  日期：2013.1.18

  A variety of N-aryl beta-nitroenamines were effectively transformed into 3-nitroindoles in good yields and with complete regioselectivity via a rapid microwave (mu V) assisted intramolecular arene alkene coupling reaction. This report further demonstrates the versatility of this method by constructing 3-carboalkozy- and 3-cyanoindoles. Optimization data, substrate scope, and applications are discussed.