N-([1,2,4]triazolo[4,3-b][1,2,4,5]tetrazin-6-yl)-4-phenylfurazan-3-amine | 1379659-23-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四嗪
• 英文名称: N-([1,2,4]triazolo[4,3-b][1,2,4,5]tetrazin-6-yl)-4-phenylfurazan-3-amine
• 英文别名: N-([1,2,4]triazolo[4,3-b][1,2,4,5]tetrazin-3-yl)-4-phenylfurazan-3-amine；4-phenyl-N-([1,2,4]triazolo[4,3-b][1,2,4,5]tetrazin-6-yl)-1,2,5-oxadiazol-3-amine
• CAS: 1379659-23-0
• 化学式: C₁₁H₇N₉O
• 分子量: 281.236
• InChiKey: ZGYDRJRPBLEDBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  4-苯基-1,2,5-恶二唑-3-胺 、 6-(3,5-dimethylpyrazol-1-yl)-1,2,4-triazolo[4,3-b][1,2,4,5]tetrazine 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以85%的产率得到N-([1,2,4]triazolo[4,3-b][1,2,4,5]tetrazin-6-yl)-4-phenylfurazan-3-amine
  参考文献：
  名称：

  A Direct Approach to a 6-Hetarylamino[1,2,4]triazolo[4,3-b][1,2,4,5]tetrazine Library

  摘要：

  The synthesis of 6-hetarylamino[1,2,4]triazolo[4,3-b][1,2,4,5]tetrazines is reported. The functionalized secondary amines were constructed via a K2CO3-mediated SNAr reaction of weakly basic hetarylamines with 3-(3,5-dimethylpyrazol-1-yl)[1,2,4]triazolo[4,3-b][1,2,4,5]tetrazines, which allowed displacement 3,5-dimethylpyrazolyl leaving group. Significantly, the reaction exhibited a broad substrate scope and proceeded in good yields.

  DOI：

  10.1021/ol403308h

文献信息

• Copper-Catalyzed C-N Coupling Reactions of Nitrogen-Rich Compounds - Reaction of Iodofurazans with s-Tetrazinylamines
  作者：Aleksei B. Sheremetev、Nadezhda V. Palysaeva、Marina I. Struchkova、Kyrill Yu. Suponitsky、Mikhail Yu. Antipin

  DOI：10.1002/ejoc.201101732

  日期：2012.4

  Access to unsymmetrical secondary dihetarylamines through the Cu(OAc)2/2-acetylcyclohexanone catalyzed cross-coupling of s-tetrazinylamines with iodofurazans has been developed. The reaction displays good functional group tolerance, involving nitro, azido, and azo groups, which are critical for the construction of energetic materials. Both 3,6-disubstituted and annelated s-tetrazines react readily

  已经开发出通过 Cu(OAc)2/2-乙酰环己酮催化的 s-四嗪基胺与碘呋咱的交叉偶联获得不对称仲二杂芳胺。该反应显示出良好的官能团耐受性，包括硝基、叠氮基和偶氮基团，这些基团对于构建含能材料至关重要。3,6-二取代和退火的 s-四嗪都容易与碘呋喃发生反应以提供所需的产品。
• A Direct Approach to a 6-Hetarylamino[1,2,4]triazolo[4,3-<i>b</i>][1,2,4,5]tetrazine Library
  作者：Nadezhda V. Palysaeva、Katerina P. Kumpan、Marina I. Struchkova、Igor L. Dalinger、Aleksandr V. Kormanov、Nataly S. Aleksandrova、Victor M. Chernyshev、Dmitrii F. Pyreu、Kyrill Yu. Suponitsky、Aleksei B. Sheremetev

  DOI：10.1021/ol403308h

  日期：2014.1.17

  The synthesis of 6-hetarylamino[1,2,4]triazolo[4,3-b][1,2,4,5]tetrazines is reported. The functionalized secondary amines were constructed via a K2CO3-mediated SNAr reaction of weakly basic hetarylamines with 3-(3,5-dimethylpyrazol-1-yl)[1,2,4]triazolo[4,3-b][1,2,4,5]tetrazines, which allowed displacement 3,5-dimethylpyrazolyl leaving group. Significantly, the reaction exhibited a broad substrate scope and proceeded in good yields.