6-amino-3-methyl-1-(4-nitrophenyl)-4-phenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile | 76973-37-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-amino-3-methyl-1-(4-nitrophenyl)-4-phenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
• 英文别名: 6-amino-3-methyl-1-(4-nitrophenyl)-4-phenyl-4H-pyrano[2,3-c]pyrazole-5-carbonitrile
• CAS: 76973-37-0
• 化学式: C₂₀H₁₅N₅O₃
• 分子量: 373.371
• InChiKey: SFOIEDIAWGHPGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-甲基-1-(4-硝基苯)-5-吡唑啉酮 在 三乙胺 作用下， 以 苯 为溶剂， 反应 2.25h， 生成 6-amino-3-methyl-1-(4-nitrophenyl)-4-phenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
  参考文献：
  名称：

  Tacconi, G.; Gatti, G.; Desimoni G., Journal fur praktische Chemie (Leipzig 1954), 1980, vol. 322, # 5, p. 831 - 834

  摘要：

  DOI：

文献信息

• Synthesis of pyranopyrazoles using isonicotinic acid as a dual and biological organocatalyst
  作者：Mohammad Ali Zolfigol、Mahsa Tavasoli、Ahmad Reza Moosavi-Zare、Parvin Moosavi、Hendrik Gerhardus Kruger、Morteza Shiri、Vahid Khakyzadeh

  DOI：10.1039/c3ra45289a

  日期：——

  In this study, a green, simple and efficient method for the preparation of 6-amino-4-(4-methoxyphenyl)-5-cyano-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazoles by means of a one-pot four component condensation reaction of aryl aldehydes, ethyl acetoacetate, malononitrile and hydrazine hydrate is reported. The reaction utilizes isonicotinic acid as a dual and biological organocatalyst at 85 °C under solvent-free conditions.

  在这项研究中，报道了一种绿色、简单且高效的方法，通过采用苯基醛、乙酰乙酸乙酯、马隆腈和水合肼的一锅四组分缩合反应制备6-amino-4-(4-methoxyphenyl)-5-cyano-3-methyl-1-phenyl-1,4-二氢吡喃[2,3-c]吡唑。这一反应在无溶剂条件下，以85 °C的温度下，采用异烟酸作为双重生物有机催化剂。
• Synthesis of 6-amino-4-(4-methoxyphenyl)-5-cyano-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazoles using disulfonic acid imidazolium chloroaluminate as a dual and heterogeneous catalyst
  作者：Ahmad Reza Moosavi-Zare、Mohammad Ali Zolfigol、Ehsan Noroozizadeh、Mahsa Tavasoli、Vahid Khakyzadeh、Abdolkarim Zare

  DOI：10.1039/c3nj00629h

  日期：——

  In this work, disulfonic acid imidazolium chloroaluminate [Dsim]AlCl4} is applied as a new acidic and heterogeneous catalyst for green, simple and efficient synthesis of 6-amino-4-(4-methoxyphenyl)-5-cyano-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazoles by the one-pot multi-component condensation of aryl aldehydes with ethyl acetoacetate, malononitrile and hydrazine hydrate at 80 °C under solvent-free conditions.

  本研究采用二磺酸咪唑鎓氯铝酸盐[Dsim]AlCl4}作为一种新型酸性异相催化剂，通过乙酰乙酸乙酯、丙二腈和芳基醛与乙酰乙酸乙酯的一锅多组分缩合反应，绿色、简单、高效地合成了6-氨基-4-(4-甲氧基苯基)-5-氰基-3-甲基-1-苯基-1、在 80 °C 无溶剂条件下，通过芳基醛与乙酰乙酸乙酯、丙二腈和水合肼的一锅多组分缩合反应，合成 6-氨基-4-(4-甲氧基苯基)-5-氰基-3-甲基-1-苯基-1,4-二氢吡喃并[2,3-c]吡唑。
• Synthesis of pyranopyrazoles using nano-Fe-[phenylsalicylaldiminemethylpyranopyrazole]Cl₂ as a new Schiff base complex and catalyst
  作者：Ahmad Reza Moosavi-Zare、Hamid Goudarziafshar、Khadijeh Saki

  DOI：10.1002/aoc.3968

  日期：2018.1

  By the condensation reaction of benzaldehyde with ethyl acetoacetate, malononitrile and hydrazine hydrate in the presence of FeCl2, a pyranopyrazole derivative was prepared which was then reacted with salicylaldehyde to afford nano‐Fe‐[phenylsalicylaldiminemethylpyranopyrazole]Cl2 (nano‐[Fe‐PSMP]Cl2). The prepared nano‐Schiff base complex was fully characterized using Fourier transform infrared spectroscopy

  在FeCl 2存在下，通过苯甲醛与乙酰乙酸乙酯，丙二腈和水合肼的缩合反应，制得吡喃并吡唑衍生物，然后使其与水杨醛反应，得到纳米级Fe- [苯基水杨基亚胺基甲基吡喃并吡唑] Cl 2（纳米-[Fe-PSMP ] Cl 2）。使用傅立叶变换红外光谱，X射线衍射，热重分析，差示热重分析，扫描电子显微镜和紫外可见光谱对所制备的纳米席夫碱复合物进行了充分表征，并用作制备吡喃并吡唑的有效催化剂。
• Copper‐immobilized ionic liquid as an alternative to organic solvents in the one‐pot synthesis of bioactive dihydropyrano[ <i>2,3‐c</i> ]pyrazole derivatives
  作者：Hossein Ghafuri、Maede Kazemnezhad Leili、Hamid Reza Esmaili Zand

  DOI：10.1002/aoc.5757

  日期：2020.9

  designed, characterized, and employed as both promoter and solvent in the synthesis of some dihydropyrano[2,3‐c]pyrazoles. The synthesized ionic liquid was characterized by 1H NMR, 13C NMR, FTIR, ICP and EDX analysis and showed high catalytic activity to proceed the synthesis of bioactive dihydropyrano[2,3‐c]pyrazole derivatives. This method has the advantage of using the IL as a green medium for the

  在这项研究中，设计，表征了一种新型的铜固定离子液体（IL），并在某些二氢吡喃并[2,3- c ]吡唑的合成中用作促进剂和溶剂。通过1 H NMR，13 C NMR，FTIR，ICP和EDX分析对合成的离子液体进行表征，并显示出高催化活性，可进行生物活性二氢吡喃并[2,3- c ]吡唑衍生物的合成。该方法的优点是使用IL作为绿色介质，可在短反应时间内以高至极好的收率合成产物。
• Uncapped SnO2 quantum dot catalyzed cascade assembling of four components: a rapid and green approach to the pyrano[2,3-c]pyrazole and spiro-2-oxindole derivatives
  作者：Sanjay Paul、Koyel Pradhan、Sirshendu Ghosh、S.K. De、Asish R. Das

  DOI：10.1016/j.tet.2014.02.077

  日期：2014.9

  A new uncapped SnO2 quantum dots (QDs) catalyzed strategy for the synthesis of substituted pyrano [2,3-c]pyrazole and spiro-2-oxindole derivatives has been developed via a multicomponent one pot approach in aqueous medium. The reactions can be performed at low catalyst loadings with excellent functional group tolerance. This communication also reports a comparative study of the efficiency related to the catalytic activity of uncapped SnO2 QDs, oleic acid capped SnO2 QDs, and SnO2 nanoflower. Uncapped SnO2 QDs, capped SnO2 QDs, and SnO2 nanoflower were prepared by simple solvothermal method and characterized by XRD, FESEM, and TEM images. The easy recovery of the catalyst and high yield of the products make the protocol attractive, sustainable, and economic. The catalyst was reused for six cycles with almost unaltered catalytic activity. (C) 2014 Elsevier Ltd. All rights reserved.