2H-Indol-2-one, 3-diazo-1,3-dihydro-5,7-dinitro- | 151797-90-9

• 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: 2H-Indol-2-one, 3-diazo-1,3-dihydro-5,7-dinitro-
• 英文别名: 3-Diazo-1,3-dihydro-5,7-dinitro-2H-indol-2-one；5,7-dinitro-3-diazo-1,3-dihydro-2H-indol-2-one
• CAS: 151797-90-9
• 化学式: C₈H₃N₅O₅
• 分子量: 249.142
• InChiKey: VJYTVVWOPUPUFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.47
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  151.78
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2H-Indol-2-one, 3-diazo-1,3-dihydro-5,7-dinitro- 、 α-(Tetrahydropyrrolylidene-2) acetate d'ethyle 以78%的产率得到
  参考文献：
  名称：

  Augusti Rodinei, Kascheres Concetta, Tetrahedron, 50 (1994) N 23, S 6723- 6726

  摘要：

  DOI：
• 作为产物：
  描述：

  5,7-dinitro-1H-indole-2,3-dione 在 对甲苯磺酰肼 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以76%的产率得到2H-Indol-2-one, 3-diazo-1,3-dihydro-5,7-dinitro-
  参考文献：
  名称：

  Reactions of 3-diazo-1,3-dihydro-2H-indol-2-one derivatives with enaminones. A novel synthesis of 1,2,3-triazoles

  摘要：

  A new and efficient method of 1,2,3-triazole synthesis is described in which these heterocyclics are formed through a novel nitrogen transfer from diazocarbonyl compounds to enaminones. Thus, the reaction of 3-diazo-1,3-dihydro-2H-indol-2-one derivatives 1 (X = NR3) and 3-diazobenzo[b]-thiophen-2(3H)-one 5 (X = S) with enaminones 2 and 7 leads to the formation of mainly 1,2,3-triazoles 4 and pyrazoloquinazolinones 3. Both the phenyl substituents (Y and Z in 1) and the nature of the X group affects the reaction rate and product distribution. Rate increases with an increase in the electron-withdrawing ability of the substituents Y and Z. The dinitro derivative 1g is shown to be the most efficient in promoting 1,2,3-triazole 4 formation while pyrazoloquinazolinones 3 are often competitively formed when other derivatives of 1 are employed.

  DOI：

  10.1021/jo00077a030
• 作为试剂：
  描述：

  4-(methylamino)-3-penten-2-one 在 2H-Indol-2-one, 3-diazo-1,3-dihydro-5,7-dinitro- 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以8%的产率得到5,7-二硝基氧化吲哚
  参考文献：
  名称：

  Reactions of 3-diazo-1,3-dihydro-2H-indol-2-one derivatives with enaminones. A novel synthesis of 1,2,3-triazoles

  摘要：

  A new and efficient method of 1,2,3-triazole synthesis is described in which these heterocyclics are formed through a novel nitrogen transfer from diazocarbonyl compounds to enaminones. Thus, the reaction of 3-diazo-1,3-dihydro-2H-indol-2-one derivatives 1 (X = NR3) and 3-diazobenzo[b]-thiophen-2(3H)-one 5 (X = S) with enaminones 2 and 7 leads to the formation of mainly 1,2,3-triazoles 4 and pyrazoloquinazolinones 3. Both the phenyl substituents (Y and Z in 1) and the nature of the X group affects the reaction rate and product distribution. Rate increases with an increase in the electron-withdrawing ability of the substituents Y and Z. The dinitro derivative 1g is shown to be the most efficient in promoting 1,2,3-triazole 4 formation while pyrazoloquinazolinones 3 are often competitively formed when other derivatives of 1 are employed.

  DOI：

  10.1021/jo00077a030

文献信息

• Bicyclic triazoles from a diazo transfer reaction between cyclic enaminones and 5,7-dinitro-3-diazo-1,3-dihydro-2H-indol-2-one
  作者：Rodinei Augusti、Concetta Kascheres

  DOI：10.1016/s0040-4020(01)81328-4

  日期：1994.1

  The synthetic usefulness of a new method of 1,2,3-triazole synthesis has been demonstrated. By employing cyclic enamino esters 3 and enamino ketones 4 in reactions with 5,7-dinitro-3-diazo-1,3-dihydro-2H-indol-2-one (1), bicyclic triazoles 5 and 6 have been prepared in good to excellent yields.

  已经证明了1,2,3-三唑合成新方法的合成有用性。通过与5，7-二硝基-3-重氮-1，3-二氢-2H-吲哚-2-酮（1）反应使用环状烯氨基酯3和烯氨基酮4，良好地制备了双环三唑5和6。达到优异的产量。