4-(4-bromophenyl)-3-methyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6(7H)-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(4-bromophenyl)-3-methyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6(7H)-one
• 英文别名: 4-(4-bromophenyl)-3-methyl-2,4,5,7-tetrahydropyrazolo[3,4-b]pyridin-6-one；4-(4-bromophenyl)-3-methyl-1,2,4,5-tetrahydropyrazolo[3,4-b]pyridin-6-one
• 化学式: C₁₃H₁₂BrN₃O
• 分子量: 306.162
• InChiKey: CFZWPQHKKZGYIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  57.8
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-氨基-5-甲基吡唑 、 5-(4-bromobenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 以 N,N-二甲基甲酰胺 为溶剂， 以76%的产率得到4-(4-bromophenyl)-3-methyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6(7H)-one
  参考文献：
  名称：

  Heterocyclizations of 5-methylpyrazol-3-amine with unsaturated arylaliphatic carboxylic acid derivatives

  摘要：

  Cyclocondensation of 5-methylpyrazol-3-amine with methyl cinnamate and arylmethylidene-malonic acids in DMF and methanol leads to the formation of 7-aryl-2-methyl-6,7-dihydropyrazolo[1,5-a]pyrimidin-5(4H)-ones. Arylmethylidenemalonic acids react with the title amine at a ratio of 1: 2 in nitrobenzene to give 4-aryl-3,5-dimethyl-1,7-dihydrodipyrazolo[3,4-b:4',3'-e]pyridines. Heterocyclizations of 5-methylpyrazol-3-amine with 5-arylmethylidene-2,2-dimethyl-1,3-dioxane-4,6-diones or their precursors, para-substituted benzaldehydes and 2,2-dimethyl-1,3-dioxane-4,6-dione (Meldrum's acid) in all solvents (methanol, DMF, and nitrobenzene) give the corresponding 4-aryl-3-methyl-2,4,5,7-tetrahydropyrazolo[3,4-b]pyridin-6-ones. The structure of 3-methyl-4-(4-nitrophenyl)-2,4,5,7-tetrahydropyrazolo[3,4-b]pyridin-6-one was proved by X-ray analysis.

  DOI：

  10.1134/s1070428006070153

文献信息

• A green, efficient and recyclable Fe+3@K10 catalyst for the synthesis of bioactive pyrazolo[3,4-b]pyridin-6(7H)-ones under "on water" conditions
  作者：Manouchehr Mamaghani、Farhad Shirini、Nosrat O. Mahmoodi、Abbas Azimi-Roshan、Hussein Hashemlou

  DOI：10.1016/j.molstruc.2013.07.060

  日期：2013.11

  Abstract An efficient regioselective one-pot three-component synthesis of 4-aryl-3-methyl-4,5-dihydro-1 H -pyrazolo[3,4-b]pyridin-6(7 H )-ones and their bis-derivatives ( Table 3 and Fig. 2 ) catalyzed by Fe +3 -K10 montmorillonite (Fe +3 @K10) under the Sharpless conditions (“On water” contdiions) is described. This rapid method produced the products in short reaction times (10–15 min) and excellent

  摘要 4-芳基-3-甲基-4,5-二氢-1 H-吡唑并[3,4-b]吡啶-6(7 H )-酮及其双-酮的高效区域选择性一锅三组分合成描述了在 Sharpless 条件（“水上”条件）下由 Fe +3 -K10 蒙脱石（Fe +3 @K10）催化的衍生物（表 3 和图 2）。这种快速方法可以在很短的反应时间（10-15 分钟）和极好的收率（87-95%）内生成产物。检查合成产物的抗菌活性。一些产品显示出有希望的活性。
• Polyethylene Glycol (PEG-400): An Efficient and Recyclable Reaction Medium for the Synthesis of Pyrazolo[3,4-b]pyridin-6(7H)-one Derivatives
  作者：Xiaoxing Zhong、Guolan Dou、Deming Wang

  DOI：10.3390/molecules181113139

  日期：——

  A mild and efficient synthesis of pyrazolo[3,4-b]pyridine-6(7H)-one derivatives via a three-component reaction of an aldehyde, Meldrum’s acid and 3-methyl-1H-pyrazol-5-amine using recyclable polyethylene glycol (PEG)-400 as a reaction medium is described. This method has the advantages of accessible starting materials, good yields, mild reaction conditions and begin environmentally friendly.

  使用可回收聚乙烯通过醛、Meldrum 酸和 3-甲基-1H-吡唑-5-胺的三组分反应温和有效地合成吡唑并[3,4-b]吡啶-6(7H)-酮衍生物描述了乙二醇 (PEG)-400 作为反应介质。该方法具有原料易得、收率好、反应条件温和、起始环境友好等优点。
• New multicomponent domino reactions (MDRs) in water: highly chemo-, regio- and stereoselective synthesis of spiro{[1,3]dioxanopyridine}-4,6-diones and pyrazolo[3,4-b]pyridines
  作者：Ning Ma、Bo Jiang、Ge Zhang、Shu-Jiang Tu、Walter Wever、Guigen Li

  DOI：10.1039/c0gc00073f

  日期：——

  multicomponent domino reactions (MDRs) have been established for the synthesis of spiropyrazolo[1,3]dioxanopyridine}-4,6-diones, spiroisoxazolo[1,3]dioxanopyridine}-4,6-diones and pyrazolo[3,4-b]pyridines. The MDRs were conducted by reacting readily available and inexpensive starting materials in aqueous solution under microwave irradiation. A total of 26 examples were examined, and showed a broad substrate

  已经建立了新的多组分多米诺反应（MDR），用于合成螺吡唑并[1,3]二恶氧吡啶} -4,6-二酮，螺异唑并[1,3]二氧杂吡啶} -4,6-二酮和吡唑并[ 3，4- b ]吡啶。通过在微波辐射下使易得且廉价的起始原料在水溶液中反应来进行MDR。总共检查了26个实例，它们显示出较宽的底物范围和较高的总收率（76-93％）。已经提出了一种新的机理来解释反应过程以及由此产生的化学，区域和立体选择性。本绿色合成方法显示出有吸引力的特性，例如使用水 作为反应介质，一锅条件，反应时间短（9-13分钟），后处理容易/纯化 且无需使用任何酸或金属助催化剂即可减少废物产生。
• Heterocyclizations of 5-methylpyrazol-3-amine with unsaturated arylaliphatic carboxylic acid derivatives
  作者：V. V. Lipson、S. M. Desenko、M. G. Shirobokova、O. V. Shishkin、S. V. Shishkina

  DOI：10.1134/s1070428006070153

  日期：2006.7

  Cyclocondensation of 5-methylpyrazol-3-amine with methyl cinnamate and arylmethylidene-malonic acids in DMF and methanol leads to the formation of 7-aryl-2-methyl-6,7-dihydropyrazolo[1,5-a]pyrimidin-5(4H)-ones. Arylmethylidenemalonic acids react with the title amine at a ratio of 1: 2 in nitrobenzene to give 4-aryl-3,5-dimethyl-1,7-dihydrodipyrazolo[3,4-b:4',3'-e]pyridines. Heterocyclizations of 5-methylpyrazol-3-amine with 5-arylmethylidene-2,2-dimethyl-1,3-dioxane-4,6-diones or their precursors, para-substituted benzaldehydes and 2,2-dimethyl-1,3-dioxane-4,6-dione (Meldrum's acid) in all solvents (methanol, DMF, and nitrobenzene) give the corresponding 4-aryl-3-methyl-2,4,5,7-tetrahydropyrazolo[3,4-b]pyridin-6-ones. The structure of 3-methyl-4-(4-nitrophenyl)-2,4,5,7-tetrahydropyrazolo[3,4-b]pyridin-6-one was proved by X-ray analysis.