6-amino-1,4-dihydro-3,4-dimethylpyrano[2,3-c]pyrazole-5-carbonitrile | 893754-30-8

• 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-1,4-dihydro-3,4-dimethylpyrano[2,3-c]pyrazole-5-carbonitrile
• 英文别名: 6-amino-3,4-dimethyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
• CAS: 893754-30-8
• 化学式: C₉H₁₀N₄O
• mdl: MFCD07365427
• 分子量: 190.205
• InChiKey: GZDATQHLOWWZQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  87.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙酰乙酸乙酯 、 乙醛 、 丙二腈 在 一水合肼 作用下， 以 水 为溶剂， 反应 1.67h， 以45%的产率得到6-amino-1,4-dihydro-3,4-dimethylpyrano[2,3-c]pyrazole-5-carbonitrile
  参考文献：
  名称：

  钛接枝的聚酰胺胺树枝状二氧化硅杂化催化剂通过双活化途径 轻松合成吡喃并吡唑和3,4-二氢嘧啶-2（1 H）-一†

  摘要：

  一种简单，高效且环保的方法，可制备具有生物活性的吡喃并吡唑和3,4-二氢嘧啶-2（1 H）-此处描述了一个。成功合成了钛接枝的聚酰胺型胺型树枝状二氧化硅杂化催化剂，并在Biginelli反应和吡喃并吡咯合成等两个重要的多组分反应中研究了其催化性能。研究表明，树枝状二氧化硅杂化催化剂的结晶孔壁结构使反应物易于吸附。二氧化硅表面的路易斯酸性和路易斯碱性相结合，有助于并加速高产率合成所需产物。本方法的关键优点是产物的优异产率，低催化剂负载，较短的反应时间，容易的后处理以及通过非色谱法纯化产物和催化剂的可重复使用性。

  DOI：

  10.1039/c5ra16723j

文献信息

• Using magnetized water as a solvent for a green, catalyst-free, and efficient protocol for the synthesis of pyrano[2,3-c]pyrazoles and pyrano[4′,3′:5,6]pyrazolo [2,3-d]pyrimidines
  作者：Mohammad Bakherad、Ali Keivanloo、Mostafa Gholizadeh、Rahele Doosti、Mohaddese Javanmardi

  DOI：10.1007/s11164-016-2680-y

  日期：2017.2

  A facile, eco-friendly, and highly efficient one-pot four-component protocol is demonstrated for the synthesis of the pyrano[2,3-c]pyrazole and pyrano[4′,3′:5,6]pyrazolo [2,3- d ]pyrimidine derivatives using magnetized water as a new green solvent. Simplicity, short reaction time, high yield, easy work-up, and absence of hazardous organic solvents are the main advantages of this method .

  已证明一种简便，环保，高效的一锅四组分方案可用于合成吡喃并[2,3-c]吡唑和吡喃并[4'，3'：5,6]吡唑并[2， 3- d ]嘧啶衍生物，使用磁化水作为新的绿色溶剂。该方法的主要优点是操作简便，反应时间短，收率高，后处理简便且无有害有机溶剂。
• Sodium gluconate: An efficient organocatalyst for the synthesis of dihydropyrano[2,3-c] pyrazole derivatives
  作者：A. Khandebharad、S. Sarda、M. Soni、B. Agrawal

  DOI：10.4314/bcse.v33i2.13

  日期：——

  Sodium gluconate presented as a category of biomolecule found to be a proficient and recyclable organocatalyst for the synthesis of dihydropyrano[2,3-c]pyrazole derivatives via one-pot multicomponent reaction of aryl aldehyde, malononitrile, ethyl acetoacetate and hydrazine hydrate in water as a solvent. The catalyst is non-toxic in nature, commercially available, biodegradable and easily separated from the reaction mixture. Present protocol avoids the use of the heavy metal catalyst, harsh reaction condition and the reusability of catalyst, broad substrate scope, simple work-up procedure and excellent yield of products make this protocol greener.

  葡萄糖酸钠作为一类生物大分子被发现是一种高效且可回收的有机催化剂，可通过芳基醛、丙二腈、乙酰乙酸乙酯和水合肼在水中的单组分反应合成二氢吡喃并[2,3-c]吡唑衍生物。催化剂无毒，可从市场上购买，可生物降解，且易于从反应混合物中分离。本方案避免了重金属催化剂的使用，避免了苛刻的反应条件，催化剂可重复使用，底物范围广，操作步骤简单，产品收率高，使本方案更加绿色环保。
• Synthesis of Dihydropyrano[2,3-C]pyrazoles Using Mandelic Acid as an Efficient Catalyst
  作者：Jitendra B. Gujar、Raghunath N. Zambare、Murlidhar S. Shingare

  DOI：10.1080/00304948.2021.2007699

  日期：2022.3.4

  (2022). Synthesis of Dihydropyrano[2,3-C]pyrazoles Using Mandelic Acid as an Efficient Catalyst. Organic Preparations and Procedures International: Vol. 54, No. 2, pp. 138-144.

  （2022 年）。以扁桃酸为高效催化剂合成二氢吡喃[2,3-C]吡唑。国际有机制剂和程序：卷。54，第 2 期，第 138-144 页。
• Solvent-free multicomponent synthesis of pyranopyrazoles: per-6-amino-β-cyclodextrin as a remarkable catalyst and host
  作者：Kuppusamy Kanagaraj、Kasi Pitchumani

  DOI：10.1016/j.tetlet.2010.04.087

  日期：2010.6

  A simple, green and efficient protocol is developed with per-6-amino-beta-cyclodextrin (per-6-ABCD) which acts simultaneously as a supramolecular host and as an efficient solid base catalyst for the solvent-free syntheses of various dihydropyrano[2,3-c]pyrazole derivatives involving a four-component reaction. This atom-economical protocol, reported for the first time with ketones also, includes a much milder procedure, does not involve any tedious work-up or purification, avoids hazardous reagents/byproducts and results in near quantitative yields. The catalyst can be reused at least six times without any change in its catalytic activity. (C) 2010 Elsevier Ltd. All rights reserved.
• A four-component synthesis of dihydropyrano[2,3-c]pyrazoles in a new water-based worm-like micellar medium
  作者：Fatemeh Tamaddon、Masoomeh Alizadeh

  DOI：10.1016/j.tetlet.2014.04.122

  日期：2014.6