1-methoxypyrido[1,2-b]indazole | 1318768-03-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并吡啶类
• 英文名称: 1-methoxypyrido[1,2-b]indazole
• CAS: 1318768-03-4
• 化学式: C₁₂H₁₀N₂O
• 分子量: 198.224
• InChiKey: XOGWRCZFIGGQED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  26.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(2-甲氧基苯基)吡啶 在 sodium azide 、 4O₄S^(2-)*Ce⁽⁴⁺⁾ 、 氧气 、 palladium diacetate 、 iron(II) chloride 作用下， 以 二甲基亚砜 为溶剂， 100.0 ℃ 、101.33 kPa 条件下， 反应 82.0h， 以70%的产率得到1-methoxypyrido[1,2-b]indazole
  参考文献：
  名称：

  Pd-Catalyzed Tandem C–H Azidation and N–N Bond Formation of Arylpyridines: A Direct Approach to Pyrido[1,2-b]indazoles

  摘要：

  A novel Pd-catalyzed nitrogenation of arylpyridines via C-H azidation has been developed. Direct C-N and N-N formations are achieved for this N-atom incorporation transformation using azides as the N-atom source. This method provides an alternatively concise approach for the construction of bioactively important pyrido[1,2-b]indazoles.

  DOI：

  10.1021/ol402060q

文献信息

• Aryne [3 + 2] cycloaddition with N-sulfonylpyridinium imides and in situ generated N-sulfonylisoquinolinium imides: a potential route to pyrido[1,2-b]indazoles and indazolo[3,2-a]isoquinolines
  作者：Jingjing Zhao、Pan Li、Chunrui Wu、Hongli Chen、Wenying Ai、Renhong Sun、Hailong Ren、Richard C. Larock、Feng Shi

  DOI：10.1039/c2ob06611d

  日期：——

  The aryne [3 + 2] cycloaddition process with pyridinium imides breaks the aromaticity of the pyridine ring. By equipping the imide nitrogen with a sulfonyl group, the intermediate readily eliminates a sulfinate anion to restore the aromaticity, leading to the formation of pyrido[1,2-b]indazoles. The scope and limitation of this reaction are discussed. As an extension of this chemistry, N-tosylisoquinolinium

  与吡啶鎓酰亚胺的芳烃[3 + 2]环加成过程破坏了吡啶环的芳香性。通过在酰亚胺氮上加成磺酰基，该中间体容易消除亚磺酸根阴离子以恢复芳香性，从而导致吡啶并[1,2- b ]吲唑的形成。讨论了该反应的范围和局限性。作为该化学反应的扩展，通过AgOTf催化的6-endo-dig亲电环化反应从N '-（2-炔基亚苄基）-甲苯磺酰肼原位生成的N-甲苯磺酰异喹啉鎓亚胺易于进行芳烃[3 + 2]环加成反应而制得吲哚唑[3,2- a同一锅中的]-异喹啉，为这些潜在的抗癌药提供了高效途径。
• Synthesis of Pyrido[1,2-<i>b</i>]indazoles via Aryne [3 + 2] Cycloaddition with <i>N</i>-Tosylpyridinium Imides
  作者：Jingjing Zhao、Chunrui Wu、Pan Li、Wenying Ai、Hongli Chen、Chaojie Wang、Richard C. Larock、Feng Shi

  DOI：10.1021/jo200863e

  日期：2011.8.19

  The [3 + 2] cycloaddition of arynes with N-tosylpyridinium imides, followed by an elimination of Ts-, affords pyrido[1,2-b]indazoles under mild reaction conditions in good yields.
• Pd-Catalyzed Tandem C–H Azidation and N–N Bond Formation of Arylpyridines: A Direct Approach to Pyrido[1,2-<i>b</i>]indazoles
  作者：Qing-Zhong Zheng、Peng Feng、Yu-Feng Liang、Ning Jiao

  DOI：10.1021/ol402060q

  日期：2013.8.16

  A novel Pd-catalyzed nitrogenation of arylpyridines via C-H azidation has been developed. Direct C-N and N-N formations are achieved for this N-atom incorporation transformation using azides as the N-atom source. This method provides an alternatively concise approach for the construction of bioactively important pyrido[1,2-b]indazoles.