4-(2-methylphenyl)-N,3-dimethyl-5-nitro-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazol-6-amine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(2-methylphenyl)-N,3-dimethyl-5-nitro-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazol-6-amine
• 英文别名: 1,4-dihydro-N,3-dimethyl-5-nitro-1-phenyl-4-o-tolylpyrano[2,3-c]pyrazol-6-amine；N,3-dimethyl-4-(2-methylphenyl)-5-nitro-1-phenyl-4H-pyrano[2,3-c]pyrazol-6-amine
• 化学式: C₂₁H₂₀N₄O₃
• 分子量: 376.415
• InChiKey: UHBALBNXEQHPFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-甲基-1-甲硫基-2-硝基乙烯胺 、 乙酰乙酸乙酯 、 2-甲基苯甲醛 、 苯肼 在 哌啶 作用下， 以 neat (no solvent) 为溶剂， 反应 2.75h， 以77%的产率得到4-(2-methylphenyl)-N,3-dimethyl-5-nitro-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazol-6-amine
  参考文献：
  名称：

  An expedient four-component domino protocol for the regioselective synthesis of highly functionalized pyranopyrazoles and chromenopyrazoles via nitroketene-N,S-acetal chemistry under solvent-free condition

  摘要：

  Combinatorial library of pyranopyrazoles and chromenopyrazoles was regioselectively synthesized in excellent yield from ethylacetoacetate, hydrazinehydrate, substituted aldehyde/salicylaldehyde with nitroketene-N,S-acetal in the presence of piperidine under solvent-free condition (SFC) in an eco-benign manner. This novel strategy excludes tedious extraction, chromatographic separation and recrystallization processes. The final product could be obtained by simple filtration by the addition of ethanol to the reaction mixture. This domino protocol generates biologically significant heterocycles with the formation of C-C, C=C, C-N, C=N, C-O bonds and one stereo-centre in a single operation via condensation/Knoevenagel/Michael/annulation sequences. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.02.019

文献信息

• Four-Component Domino Strategy for the Combinatorial Synthesis of Novel 1,4-Dihydropyrano[2,3-<i>c</i>]pyrazol-6-amines
  作者：Selvaraj Kanchithalaivan、Sathiyamoorthi Sivakumar、Raju Ranjith Kumar、Palani Elumalai、Qazi Naveed Ahmed、Anil K. Padala

  DOI：10.1021/co4000997

  日期：2013.12.9

  An efficient one-pot four-component domino protocol for the combinatorial synthesis of novel 1,4-dihydropyrano[2,3-c]pyrazol-6-amines has been achieved. This transformation presumably occurs via cyclization- Knoevenagel condensation-Michael addition-tautomerism- intramolecular O-cyclization-elimination sequence of reactions. The significant features of this reaction include expedient one-pot process, short reaction time, no column chromatographic purification, excellent yield, and readily available starting materials.
• An expedient four-component domino protocol for the regioselective synthesis of highly functionalized pyranopyrazoles and chromenopyrazoles via nitroketene-N,S-acetal chemistry under solvent-free condition
  作者：Kamalraja Jayabal、Thirumalai Perumal Paramasivan

  DOI：10.1016/j.tetlet.2014.02.019

  日期：2014.3

  Combinatorial library of pyranopyrazoles and chromenopyrazoles was regioselectively synthesized in excellent yield from ethylacetoacetate, hydrazinehydrate, substituted aldehyde/salicylaldehyde with nitroketene-N,S-acetal in the presence of piperidine under solvent-free condition (SFC) in an eco-benign manner. This novel strategy excludes tedious extraction, chromatographic separation and recrystallization processes. The final product could be obtained by simple filtration by the addition of ethanol to the reaction mixture. This domino protocol generates biologically significant heterocycles with the formation of C-C, C=C, C-N, C=N, C-O bonds and one stereo-centre in a single operation via condensation/Knoevenagel/Michael/annulation sequences. (c) 2014 Elsevier Ltd. All rights reserved.