5-ethyl-N-(5-ethyl-3-(3-nitropyridin-2-yl)-1,3,4-thiadiazol-2(3H)-ylidene)-1,3,4-thiadiazol-2-amine | 1420066-38-1

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 5-ethyl-N-(5-ethyl-3-(3-nitropyridin-2-yl)-1,3,4-thiadiazol-2(3H)-ylidene)-1,3,4-thiadiazol-2-amine
• 英文别名: 5-ethyl-N-(5-ethyl-1,3,4-thiadiazol-2-yl)-3-(3-nitropyridin-2-yl)-1,3,4-thiadiazol-2-imine
• CAS: 1420066-38-1
• 化学式: C₁₃H₁₃N₇O₂S₂
• 分子量: 363.424
• InChiKey: ZSQLANYXVQSSSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  166
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-氨基-5-乙基-1,3,4-噻二唑 、 2-氯-3-硝基吡啶 以 甲苯 为溶剂， 反应 16.0h， 以52%的产率得到5-ethyl-N-(5-ethyl-3-(3-nitropyridin-2-yl)-1,3,4-thiadiazol-2(3H)-ylidene)-1,3,4-thiadiazol-2-amine
  参考文献：
  名称：

  Direct access to 1-aryl-5-amino-1,2,4-triazoles and [1,2,4]triazolo[1,5-a]pyridines by two new single-step reactions from 1,3,4-thiadiazol-2-amines

  摘要：

  Two new single-step reactions allowing the construction of two heterocyclic motifs are reported. Both processes involve 5-substituted 1,3,4-thiadiazol-2-amines as starting materials. Reaction with 1-fluoro-2-nitrobenzenes in presence of Hunig's base permitted the convenient synthesis of various 3-substituted 1-aryl-5-amino-1,2,4-triazoles. Reaction with 2-chloro-3-nitropyridines and 2-chloro-5-nitropyridines in similar conditions readily gave access to a number of [1,2,4]triazolo[1,5-a]pyridines. In absence of base, adducts composed by one aromatic unit and two thiadiazole units were formed. This observation and previous work by Anders and co-workers led to the suggestion of plausible mechanisms for these reactions. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.11.101

文献信息

• Direct access to 1-aryl-5-amino-1,2,4-triazoles and [1,2,4]triazolo[1,5-a]pyridines by two new single-step reactions from 1,3,4-thiadiazol-2-amines
  作者：Oscar Mammoliti、Evelyne M. Quinton、Kristof T.J. Loones、Anh Tho Nguyen、Johan Wouters、Guy Van Lommen

  DOI：10.1016/j.tet.2012.11.101

  日期：2013.2

  Two new single-step reactions allowing the construction of two heterocyclic motifs are reported. Both processes involve 5-substituted 1,3,4-thiadiazol-2-amines as starting materials. Reaction with 1-fluoro-2-nitrobenzenes in presence of Hunig's base permitted the convenient synthesis of various 3-substituted 1-aryl-5-amino-1,2,4-triazoles. Reaction with 2-chloro-3-nitropyridines and 2-chloro-5-nitropyridines in similar conditions readily gave access to a number of [1,2,4]triazolo[1,5-a]pyridines. In absence of base, adducts composed by one aromatic unit and two thiadiazole units were formed. This observation and previous work by Anders and co-workers led to the suggestion of plausible mechanisms for these reactions. (C) 2012 Elsevier Ltd. All rights reserved.