6-ethynylcinnoline

• 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: 6-ethynylcinnoline
• 英文别名: 6-Ethynylcinnoline
• 化学式: C₁₀H₆N₂
• 分子量: 154.171
• InChiKey: LARYXSWVNFPACN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4 -溴- 2 - 碘苯甲胺 在 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 三乙胺 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 水 、 邻二氯苯 、 乙腈 为溶剂， 反应 10.5h， 生成 6-ethynylcinnoline
  参考文献：
  名称：

  Cyclization of 1-(2-Alkynylphenyl)-3,3-dialkyltriazenes:  A Convenient, High-Yield Synthesis of Substituted Cinnolines and Isoindazoles

  摘要：

  A new route to isoindazoles and cinnolines through the cyclization of (2-alkynylphenyl)triazenes under neutral conditions is presented. The products that result from heating the starting triazenes depend on both the type of alkyne ortho to the triazene functionality and the temperature used. Butadiyne moieties ortho to dialkyltriazenes yield bis-isoindazole dimers when heated to 150 degreesC in MeI. A requirement for cyclization in MeI is that the (2-alkynylphenyl)triazene must contain a suitably electron-withdrawing substituent on the phenyl ring to deactivate the triazene toward methylation-induced decomposition to an iodoarene. Ethynyl moieties ortho to dialkyltriazenes yield both isoindazole dimers as well as 3-formylisoindazoles when subjected to the same conditions. Replacing MeI with 1,2-dichlorobenzene as solvent allows for the general cyclization of (2-ethynylphenyl)dialkyltriazenes. Heating to 170 degreesC results in a mixture of isoindazole and cinnoline products, whereas the cinnolines are produced exclusively in high yield at 200 degreesC. Alternatively, the isoindazoles can be obtained in good to excellent yield by stirring a 1,2-dichloroethane solution of the starting triazene with CuCl overnight at 50 degreesC.

  DOI：

  10.1021/jo020229s

文献信息

• Thermal Cyclization of (2-Ethynylphenyl)triazenes:  Facile Synthesis of Substituted Cinnolines and Isoindazoles
  作者：David B. Kimball、Austin G. Hayes、Michael M. Haley

  DOI：10.1021/ol006517x

  日期：2000.11.1

  [GRAPHICS]High-temperature intramolecular cyclization of N,N-dialkyl-N'-(4-substituted-2-ethynylphenyl)triazines provides under neutral conditions both 6-substituted cinnolines and 5-substituted isoindazoles in moderate to excellent yields.
• Cyclization of 1-(2-Alkynylphenyl)-3,3-dialkyltriazenes:  A Convenient, High-Yield Synthesis of Substituted Cinnolines and Isoindazoles
  作者：David B. Kimball、Timothy J. R. Weakley、Michael M. Haley

  DOI：10.1021/jo020229s

  日期：2002.9.1

  A new route to isoindazoles and cinnolines through the cyclization of (2-alkynylphenyl)triazenes under neutral conditions is presented. The products that result from heating the starting triazenes depend on both the type of alkyne ortho to the triazene functionality and the temperature used. Butadiyne moieties ortho to dialkyltriazenes yield bis-isoindazole dimers when heated to 150 degreesC in MeI. A requirement for cyclization in MeI is that the (2-alkynylphenyl)triazene must contain a suitably electron-withdrawing substituent on the phenyl ring to deactivate the triazene toward methylation-induced decomposition to an iodoarene. Ethynyl moieties ortho to dialkyltriazenes yield both isoindazole dimers as well as 3-formylisoindazoles when subjected to the same conditions. Replacing MeI with 1,2-dichlorobenzene as solvent allows for the general cyclization of (2-ethynylphenyl)dialkyltriazenes. Heating to 170 degreesC results in a mixture of isoindazole and cinnoline products, whereas the cinnolines are produced exclusively in high yield at 200 degreesC. Alternatively, the isoindazoles can be obtained in good to excellent yield by stirring a 1,2-dichloroethane solution of the starting triazene with CuCl overnight at 50 degreesC.