3-chloro-2-ethyl-6-nitro-2H-indazole

• 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: 3-chloro-2-ethyl-6-nitro-2H-indazole
• 英文别名: 3-Chloro-2-ethyl-6-nitro-2H-indazole；3-chloro-2-ethyl-6-nitroindazole
• 化学式: C₉H₈ClN₃O₂
• 分子量: 225.634
• InChiKey: WGNTZSGMWVSNRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  63.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-chloro-2-ethyl-6-nitro-2H-indazole 、 2,5-己二酮 在 溶剂黄146 、 tin(ll) chloride 作用下， 以 四氢呋喃 为溶剂， 以74%的产率得到3-chloro-6-(2,5-dimethyl-pyrrol-1-yl)-2-ethyl-2H-indazole
  参考文献：
  名称：

  One-pot synthesis of new 6-pyrrolyl- N -alkyl-indazoles from reductive coupling of N -alkyl-6-nitroindazoles and 2,5-hexadione

  摘要：

  One-pot synthesis of 6-pyrrolyl-N-alkyl-indazoles by the reductive coupling of N-alkyl-6-nitroindazoles and 2,5-hexadione was investigated in the presence of different reducing agents (SnCl2/AcOH and In/AcOH in THF). Indazoles 5a-h and 6a-h were obtained in good to excellent yields (74-95%) and characterized by elemental analysis, NMR, and single crystal X-ray diffraction. The same synthetic approach was also used to obtain 5-pyrrolyl-N-alkyl-indazoles. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.11.071
• 作为产物：
  描述：

  3-氯-6-硝基-1H-吲唑 、 碘乙烷 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以64%的产率得到3-chloro-1-ethyl-6-nitro-1H-indazole
  参考文献：
  名称：

  One-pot synthesis of new 6-pyrrolyl- N -alkyl-indazoles from reductive coupling of N -alkyl-6-nitroindazoles and 2,5-hexadione

  摘要：

  One-pot synthesis of 6-pyrrolyl-N-alkyl-indazoles by the reductive coupling of N-alkyl-6-nitroindazoles and 2,5-hexadione was investigated in the presence of different reducing agents (SnCl2/AcOH and In/AcOH in THF). Indazoles 5a-h and 6a-h were obtained in good to excellent yields (74-95%) and characterized by elemental analysis, NMR, and single crystal X-ray diffraction. The same synthetic approach was also used to obtain 5-pyrrolyl-N-alkyl-indazoles. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.11.071

文献信息

• Synthesis and biological evaluation against <i>Leishmania donovani</i> of novel hybrid molecules containing indazole-based 2-pyrone scaffolds
  作者：M. El Ghozlani、L. Bouissane、M. Berkani、S. Mojahidi、A. Allam、C. Menendez、S. Cojean、P. M. Loiseau、M. Baltas、E. M. Rakib

  DOI：10.1039/c8md00475g

  日期：——

  A series of novel indazole–pyrone hybrids are synthesized and tested in vitro against both Leishmania donovani axenic and intramacrophage amastigotes.

  合成了一系列新型吲唑-吡喃酮杂交化合物，并对其进行了针对唐氏利什曼原虫轴突和滋养体内变形虫的体外测试。
• One-pot synthesis of new 6-pyrrolyl- N -alkyl-indazoles from reductive coupling of N -alkyl-6-nitroindazoles and 2,5-hexadione
  作者：Mohamed El Ghozlani、Hakima Chicha、Najat Abbassi、Mohamed Chigr、Lahcen El Ammari、Mohamed Saadi、Domenico Spinelli、El Mostapha Rakib

  DOI：10.1016/j.tetlet.2015.11.071

  日期：2016.1

  One-pot synthesis of 6-pyrrolyl-N-alkyl-indazoles by the reductive coupling of N-alkyl-6-nitroindazoles and 2,5-hexadione was investigated in the presence of different reducing agents (SnCl2/AcOH and In/AcOH in THF). Indazoles 5a-h and 6a-h were obtained in good to excellent yields (74-95%) and characterized by elemental analysis, NMR, and single crystal X-ray diffraction. The same synthetic approach was also used to obtain 5-pyrrolyl-N-alkyl-indazoles. (C) 2015 Elsevier Ltd. All rights reserved.