6'-amino-1,3'-dimethyl-2-oxo-1'H-spiro[indoline-3,4'-pyrano[2,3-c]pyrazole]-5'-carbonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 6'-amino-1,3'-dimethyl-2-oxo-1'H-spiro[indoline-3,4'-pyrano[2,3-c]pyrazole]-5'-carbonitrile
• 英文别名: 6′-amino-1,3′-dimethyl-2-oxo-1′H-spiro[indoline-3,4′-pyrano[2,3-c]pyrazole]-5′-carbonitrile；6-amino-1',3-dimethyl-2'-oxospiro[2H-pyrano[2,3-c]pyrazole-4,3'-indole]-5-carbonitrile
• 化学式: C₁₆H₁₃N₅O₂
• 分子量: 307.312
• InChiKey: RXQWFVLFADSNFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(1-Methyl-2-oxo-1,2-dihydro-indol-3-ylidene)-malononitrile 、 3-甲基-2-吡唑啉-5-酮 在 三乙醇胺 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以56%的产率得到6'-amino-1,3'-dimethyl-2-oxo-1'H-spiro[indoline-3,4'-pyrano[2,3-c]pyrazole]-5'-carbonitrile
  参考文献：
  名称：

  Synthesis and molecular structure of spirocyclic 2-oxindole derivatives of 2-amino-4H-pyran condensed with the pyrazolic nucleus

  摘要：

  4,3'-Spiro[(6-amino-5-R-3-methyl-2H,4H-pyrano[2,3-c]pyrazolo)-2'-oxindoles] were synthesized based on the three-component condensation of isatins with 3-methyl-pyrazolone-5 and respective methylene active nitriles in the presence of basic catalysts. The molecular structure of the resulting compounds was proved unambiguously by X-ray diffraction. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.08.050

文献信息

• Synthesis of functionalized chromene and spirochromenes using l -proline-melamine as highly efficient and recyclable homogeneous catalyst at room temperature
  作者：Sakkani Nagaraju、Banoth Paplal、Kota Sathish、Santanab Giri、Dhurke Kashinath

  DOI：10.1016/j.tetlet.2017.09.060

  日期：2017.11

  commercially cheap l-proline and melamine for the synthesis of chromenes and spirochromenes (spirooxindoles) via multicomponent reactions at room temperature. Systematic studies were conducted in order to achieve desired reactivity and recyclability of the catalyst using various α-amino acids and aromatic amines as donor-acceptor pairs. Among the screened combinations, l-proline and melamine (3:1 ratio;

  使用便宜的1-脯氨酸和三聚氰胺开发了一种有效且可循环使用的均相催化剂，用于在室温下通过多组分反应合成色烯和螺环色酮（螺并辛多烯）。为了使用各种α-氨基酸和芳族胺作为供体-受体对，进行系统研究以实现所需的反应性和催化剂的可回收性。在筛选的组合中，l脯氨酸和三聚氰胺（3：1的比例；占总重量的3 mol％）被认为是最佳的催化剂，可以在室温下非常短的时间内（1-15分钟）以优异的产率（高达99％）提供所需的产品在DMSO中作为溶剂。通过添加EtOAc来回收催化剂，并且在不损失催化活性的情况下重复使用多达5个循环。
• Tris-hydroxymethylaminomethane (THAM): An efficient organocatalyst in diversity-oriented and environmentally benign synthesis of spirochromenes
  作者：Supriya S. Khot、Prashant V. Anbhule、Uday V. Desai、Prakash P. Wadgaonkar

  DOI：10.1016/j.crci.2018.05.005

  日期：2018.9

  Résumé Tris-hydroxymethylaminomethane has been demonstrated to be an efficient organocatalyst in diversity-oriented synthesis of medicinally prevalent spirochromenes by one-pot, three-component reactions between isatins, malononitrile, and enolizable CH acids like dimedone, 4-hydroxycoumarin, 4-hydroxy-N-methylquinolin-2-one, or in situ generated 2-methylpyrazolon-2-one. Biodegradability and extremely low cost of the catalyst are the noteworthy features of this chromatography-free protocol. Supplementary Materials: Supplementary material for this article is supplied as a separate file: mmc1.pdf

  中文翻译结果： **摘要** 三羟甲基氨基甲烷已被证明是一种高效的非金属催化剂，通过一锅三组分反应，在药物学上重要的螺色满合成中，它能够催化靛红、丙二腈与可烯醇化的CH酸（如二甲代苯二酮、4-羟基香豆素、4-羟基-N-甲基喹啉-2-酮或现场生成的2-甲基吡唑-2-酮）之间的反应。该无色谱纯化工艺的显著特点是催化剂的生物降解性和极低的成本。 **补充材料** 本文的补充材料作为一个单独的文件提供：mmc1.pdf
• Efficient four-component synthesis of spiroindole derivatives catalysed by a versatile and reusable nano-paramagnetic catalyst
  作者：Seyedeh Fatemeh Hojati、Amir Hassan Amiri、Hamideh Raouf

  DOI：10.1002/aoc.3595

  日期：2017.5

  A simple, efficient and environmentally benign route was developed for the preparation of spiro(indoline‐3,4‐pyrano[2,3‐c]pyrazole) derivatives with good yields from condensation of isatins, malononitrile (or ethyl cyanoacetate), hydrazine hydrate and ethyl acetoacetate catalysed by PFu@Fe3O4 nanocomposite. The use of easily available catalyst, shorter reaction times, better yields, simplicity of reaction

  开发了一种简单，高效且环境友好的方法，用于制备螺（吲哚啉-3,4-吡喃并[2,3- c ]吡唑）衍生物，其得自靛红，丙二腈（或氰基乙酸乙酯），水合肼的缩合反应PFu @ Fe 3 O 4纳米复合材料催化乙酰乙酸乙酯。该方法的优点是易于获得的催化剂，较短的反应时间，更高的产率，反应的简便性，非均相系统和后处理的优点。使用傅里叶变换红外光谱，X射线衍射和透射电子显微镜对催化剂进行表征。
• Ionic Liquid for One-pot Synthesis of Spiro[indoline-3,4′-pyrano[2,3-<i>c</i>]pyrazoles]
  作者：S. F. Hojati、H. Raouf

  DOI：10.1080/00304948.2016.1234824

  日期：2016.11

  ([Et3NH][AcO]) as a green catalyst for the multi-component synthesis of spiro[indoline-3,40-pyrano[2,3-c]pyrazoles]from isatin, malononitrile, ethyl acetoacetate and hydrazine (Scheme 1). The reaction of isatin (1 mmol), malononitrile (1 mmol), ethyl acetoacetate (1.1 mmol) and hydrazine hydrate (1.1 mmol) in the presence of various ionic liquid catalysts such as [Et3NH][HCOO], [Et3NH][HSO4], [Et3NH][NO3]

  吲哚核是一种重要的杂环支架，因为它存在于多种具有生物和药学活性的天然产物中。还发现 C-3 取代的螺吲哚衍生物构成了许多生物活性化合物的核心结构，这些化合物显示出增强的药物特性，例如麻醉作用和哺乳动物细胞周期的抑制作用。吡喃并[2,3-c]吡唑也是一类对药物化学家有吸引力的杂环，因为它结合了两个生物活性部分，吡喃和吡唑。据报道，它们还具有生物活性，例如抗炎、抗癌、杀虫、抗微生物作用，并且是人类 Chk1 激酶的抑制剂。过去几年，相当多的努力致力于合成多功能螺[二氢吲哚并吡唑]。制备这些杂环的最通用方法通常涉及多组分反应 (MCR)。从而避免复杂的后处理程序并使反应环保且经济可行。已经开发了许多方法用于通过靛红、丙二腈和吡唑啉-5-酮的 MCR 缩合制备螺[indoline-3,40-pyrano[2,3-c]pyrazoles]，使用各种试剂和条件，例如Et3N、17 NaHCO3 通过研磨、
• ZrO₂ nanoparticles as a reusable solid dual acid–base catalyst for facile one-pot synthesis of multi-functionalized spirooxindole derivatives under solvent free condition
  作者：Chandan Bodhak、Ashis Kundu、Animesh Pramanik

  DOI：10.1039/c5ra16259a

  日期：——

  A two-step one-pot protocol for the facile synthesis of biologically important spirooxindole derivatives such as spiro[4H-pyran-3,3′-oxindoles] and spiro[indoline-3,4′(1H′)-pyrano-[2,3-c]pyrazol-2-ones has been developed. In this method ZrO2 nanoparticles have been utilized as a reusable solid dual acid–base catalyst to get quick access to the multi-functionalized spirooxindole derivatives under solvent

  两步一锅操作方案，可轻松合成生物学上重要的螺氧杂吲哚衍生物，例如spiro [4 H -pyran -3,3'-oxindoles]和螺螺[indoline-3,4'（1 H '）-pyrano-已经开发了[2，3 - c ]吡唑-2-酮。在这种方法中，ZrO 2纳米颗粒已被用作可重用的固体双酸碱催化剂，可在室温下在无溶剂条件下快速获得多功能的螺氧杂吲哚衍生物。该方法的主要优点是操作简便，减少反应时间，消除溶剂，产品收率高，后处理程序方便以及使用无毒且可回收的ZrO 2纳米催化剂。所有这些因素使本方法经济，绿色和可持续。