Indazolo<2,1-a>indazol-6,12-dion | 18428-89-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 英文名称: Indazolo<2,1-a>indazol-6,12-dion
• 英文别名: Indazolo<2.1-a>indazol-dion-(6.12)；6H,12H-Indazolo[2,1-a]indazole-6,12-dione；indazolo[2,1-a]indazole-6,12-dione
• CAS: 18428-89-2
• 化学式: C₁₄H₈N₂O₂
• 分子量: 236.23
• InChiKey: DQNLBWPKWXWODM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为产物：
  描述：

  2-(2'-nitrophenyl)-3,1-benzoxazin-4-one 在 亚磷酸三乙酯 作用下， 以 xylene 为溶剂， 反应 20.0h， 以87%的产率得到Indazolo<2,1-a>indazol-6,12-dion
  参考文献：
  名称：

  Synthesis of Polynuclear Heterocycles; Part 5¹. New Selective Methods for the Synthesis of Indazolo[2,3-a][3,1]benzoxazin-5-ones and Indazolo [2,1-g]indazole-6,12-diones

  摘要：

  DOI：

  10.1055/s-1980-29027

文献信息

• Palladium-catalysed transfer hydrogenation of aromatic nitro compounds — an unusual chain elongation
  作者：János Németh、Árpád Kiss、Zoltán Hell

  DOI：10.1016/j.tetlet.2013.08.123

  日期：2013.11

  Aromatic nitro compounds are reduced via transfer hydrogenation in the presence of palladium on magnesium-lanthanum mixed oxide support in ethanol yielding the corresponding amines. With several acetophenone derivatives, the reduction was accompanied by chain elongation whilst the carbonyl group remained intact.

  在钯在乙醇中的镁-镧混合氧化物载体上存在钯时，通过转移氢化还原芳香族硝基化合物，得到相应的胺。对于几种苯乙酮衍生物，还原反应伴随着链延长，而羰基保持完整。
• The relationship of bisanthranil to its structural isomer and related compounds
  作者：G. K. J. Gibson、A. S. Lindsey、H. M. Paisley

  DOI：10.1039/j39670001792

  日期：——

  A spectroscopic, mass spectroscopic, and chemical examination of bisanthranil, m. p. 185°, and of its structural isomer, m. p. 302°, has confirmed the lactone structure of the former and the amide structure of the latter. The spectra were compared with those of 2-phenylindazol-3-one, 2-(2-carboxyphenyl)indazol-3-one, 2-phenyl-3,1-benzoxazin-4-one, isatoic anhydride, and dianthranilide.

  光谱分析，质谱分析和化学检测联苯乙腈，mp 185°及其结构异构体mp 302°，已确认前者的内酯结构和后者的酰胺结构。将该光谱与2-苯基吲哚-3-酮，2-（2-羧苯基）吲唑-3-酮，2-苯基-3,1-苯并恶嗪-4-酮，异丙酸酐和二蒽酰苯胺的光谱进行比较。
• Stabilizing and Activating Nitrogen Catenates
  作者：D. Scott Bohle、Zhijie Chua、Maya Singer Hobbs、Inna Perepichka、Alexander Waked

  DOI：10.1002/chem.201501241

  日期：2015.9.21

  ring‐extrusion of dinitrogen from the Dimroth intermediate to generate chelating σ‐aryls. The catenated nitrogen species can be stabilized by incorporating strong formal sp2sp2 NN σ bonds with orthogonal orientations. Extending these stabilization and activation principles may allow these types of nitrogen catenates to be useful synthons for other polyaza species.

  在双（benzotriazene -4-酮）的显着的稳定链中的六氮链在结构上，从理论上说，与光谱特征来说明中央n的耐久性该六偶氮链中的N键。该物种的反应说明了这些氮链烯酸酯通过热氮排阻或捕集单个开环的Dimroth中间体制备其他稠合杂环（如双吡唑酮）的潜力。在后面的这些反应中，2-萘甲酸根阴离子与双（苯并三氮杂-4-酮）缩合，以捕集并保留作为分离的重氮产物的两性离子重氮鎓中间体，而过渡金属则对Dimroth中间体中的二氮环挤出环产生螯合σ-芳基 该链中的氮物种可以通过将强正式SP被稳定2  SP 2 Ñ Nσ键具有正交方向。扩展这些稳定和活化原理可以使这些类型的氮链烯成为其他聚氮杂物种有用的合成子。
• One‐Pot Manganese (I)‐Catalyzed Oxidant‐Controlled Divergent Functionalization of 2‐Arylindazoles
  作者：Krishna Kanta Das、Asim Kumar Ghosh、Alakananda Hajra

  DOI：10.1002/chem.202302849

  日期：2024.1.16

  The oxidant‐controlled divergent synthesis of C‐2′ formyl 2H‐indazoles and indazoloindazolediones has been developed through Mn(I)‐ catalyzed ortho C−H functionalization of 2H‐indazoles with para‐formaldehyde to afford C‐2′ hydroxymethylated 2H‐indazoles and subsequently oxidation with varying the amount of DDQ in one‐pot. By employing selectfluor as the oxidant instead of DDQ, this reaction exclusively provided indazolebenzoxazine derivatives. This strategy delivered unsymmetrical indazoloindazoledione and indazolobenzoxazine with varied functional group tolerance in moderate to good yields.

  摘要 通过锰(I)催化 2H-indazoles 与对甲醛的正交 C-H 功能化，得到 C-2′ 羟甲基化的 2H-indazoles ，然后用不同量的 DDQ 进行氧化，开发了氧化剂控制的 2H-indazoles 和吲唑吲哚二酮的分歧合成。通过使用选择氟代替 DDQ 作为氧化剂，该反应只提供了吲唑-苯并恶嗪衍生物。这一策略以中等至良好的产率获得了具有不同官能团耐受性的不对称吲唑吲唑二酮和吲唑苯并恶嗪。
• Role of intermolecular reactions in thermolysis of aromatic nitro compounds in supercritical aromatic solvents
  作者：Leanna M. Minier、Kay R. Brower、Jimmie C. Oxley

  DOI：10.1021/jo00010a025

  日期：1991.5

  Several nitroarenes were decomposed isothermally in dilute supercritical solution in benzene or toluene and in the vapor phase in the temperature range of 290-380-degrees-C in sealed glass tubes with pressures up to 100 MPa. The mechanisms of thermolysis are inferred from kinetic studies and product analysis. The initial rate-controlling step for nitrobenzene and p-nitrotoluene decomposition is probably intermolecular hydrogen abstraction to form an ArNO2H radical intermediate. The nature of the transition state is deduced from the activation volume (DELTA-V*), H/D kinetic-isotope effect, and a linear free-energy relationship between the ionization potential of the hydrogen donor and the logarithm of the decomposition rate. A concurrent pathway for o-nitrotoluene is an intramolecular reaction in which anthranil is an intermediate. The behavior of 1,3-dinitrobenzene and 1,4-dinitrobenzene resembles that of nitrobenzene, whereas 2,4-dinitrotoluene and 2,6-dinitrotoluene decompose in the same manner as o-nitrotoluene. Activation parameters are given and detailed mechanisms proposed.