3-Methyl-4-[4-(dimethylamino)phenyl]-4,5-dihydro-1H-pyrazolo[3,4-b]pyridine-6(7H)-one | 937389-23-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-Methyl-4-[4-(dimethylamino)phenyl]-4,5-dihydro-1H-pyrazolo[3,4-b]pyridine-6(7H)-one
• 英文别名: 4-[4-(dimethylamino)phenyl]-3-methyl-2,4,5,7-tetrahydropyrazolo[3,4-b]pyridin-6-one
• CAS: 937389-23-6
• 化学式: C₁₅H₁₈N₄O
• 分子量: 270.334
• InChiKey: RAXIWSHUJHLIDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  丙二酸环(亚)异丙酯 、 3-氨基-5-甲基吡唑 、 对二甲氨基苯甲醛 在 Fe+3(at)K₁₀ catalyst 作用下， 以 水 为溶剂， 反应 0.17h， 以94%的产率得到3-Methyl-4-[4-(dimethylamino)phenyl]-4,5-dihydro-1H-pyrazolo[3,4-b]pyridine-6(7H)-one
  参考文献：
  名称：

  一种绿色、高效、可回收的 Fe+3@K10 催化剂，用于在“水上”条件下合成具有生物活性的吡唑并[3,4-b]吡啶-6(7H)-酮

  摘要：

  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。

  DOI：

  10.1016/j.molstruc.2013.07.060

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。
• A new nano-Fe₃O₄-supported organocatalyst based on 3,4-dihydroxypyridine: an efficient heterogeneous nanocatalyst for one-pot synthesis of pyrazolo[3,4-<i>b</i>]pyridines and pyrano[2,3-d]pyrimidines
  作者：Mozhgan Pirhayati、Ali Kakanejadifard、Hojat Veisi

  DOI：10.1002/aoc.3534

  日期：2016.12

  Meldrum's acid and 5‐methylpyrazol‐3‐amine under very mild reaction condition and in the presence of ethanol solvent. Moreover, the synthesized catalyst was used for one‐pot, three‐component condensation of aromatic aldehydes with barbituric acid and malononitrile to produce 7‐amino‐2,4‐dioxo‐5‐phenyl‐2,3,4,5‐tetrahydro‐1H‐pyrano[2,3‐d]pyrimidine‐6‐carbonitriles. All reactions are completed in short

  已经开发了一种简单实用的策略，用于合成基于3,4-二羟基吡啶（Fe 3 O 4 / Py）的新型纳米Fe 3 O 4负载的有机催化剂体系。使用傅立叶变换红外光谱，透射和扫描电子显微镜，X射线衍射，振动样品磁力分析和能量色散X射线分析对制备的催化剂进行了表征。因此，Fe 3 O 4 / Py纳米颗粒表现出超顺磁性，饱和磁化强度为61 emug -1，表明其在磁分离技术中的潜在应用。我们的实验结果表明，吡啶官能化的Fe 3O 4纳米颗粒是一种非常有效的碱催化剂，可在非常温和的反应条件下，在乙醇溶剂的存在下，对各种芳族醛，Meldrum的酸和5-甲基吡唑-3-胺进行多米诺骨牌缩合。此外，合成的催化剂还用于芳香醛与巴比妥酸和丙二烯的一锅三组分缩合反应，生成7-氨基-2,4-二氧杂-5-5-苯基-2,3,4,5-四氢1 H-吡喃并[2,3 - d ]嘧啶-6-腈。所有反应均在短时间内完成，并且获得的
• Mesoporous SBA-15 Silica Phenylsulfonic Acid (SBA-15-Ph-SO₃H) as Efficient Nanocatalyst for One-pot Three-component Synthesis of 3-Methyl-4-aryl-2,4,5,7-tetrahydropyrazolo[3,4-b]pyridine-6-ones
  作者：Hojat Veisi、Malak Hekmati、Saba Hemmati

  DOI：10.1002/jhet.2689

  日期：2017.3

  A simple, economical, and efficient approach to the one‐pot synthesis of 3‐methyl‐4‐aryl‐2,4,5,7‐tetrahydropyrazolo[3,4‐b]pyridine‐6‐ones by multicomponent assembling of 5‐methylpyrazol‐3‐amine, aldehydes, and Meldrum's acid using mesoporous silica phenylsulfonic acid (SBA‐15‐Ph‐SO3H) as recyclable and heterogonous solid acid nanocatalyst has been described. This protocol has the advantages of high

  一种简单，经济，有效的方法，可通过5-组分的多组分组装法一锅合成3-甲基-4-芳基-2,4,5,7-四氢吡唑并[3,4-b]吡啶-6-酮已经描述了使用介孔二氧化硅苯磺酸（SBA-15-Ph-SO 3 H）作为可循环利用的多边固体酸纳米催化剂的甲基吡唑-3-胺，醛和梅德鲁姆酸。该协议具有产量高，适用范围广，环境友好的优点。
• An efficient regioselective sonochemical synthesis of novel 4-aryl-3-methyl-4,5-dihydro-1H-pyrazolo[3,4-b]pyridin-6(7H)-ones
  作者：Abbas Azimi Roshan、Manouchehr Mamaghani、Nosrat Ollah Mahmoodi、Farhad Shirini

  DOI：10.1016/j.cclet.2011.12.009

  日期：2012.4

  An efficient ultrasound-assisted preparation of a series of novel 4-aryl-3-methyl-4,5-dihydro-1H-pyrazclo[3,4-b]pyridin-6(7H)ones via the reaction of 5-amino-3-methyl-1H-pyrazole, Meldrum's acid and various arylaldehydes using one-pot three-component approach is described. This rapid method produced the products in short reaction times (3-4 min) and excellent yields (87-95%). (C) 2011 Manouchehr Mamaghani. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• 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.