ethyl 7'-amino-5-chloro-2,2',4'-trioxo-1',2',3',4'-tetrahydrospiro[indoline-3,5'-pyrano[2,3-d]pyrimidine]-6'-carboxylate | 1380401-50-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃嘧啶类
• 英文名称: ethyl 7'-amino-5-chloro-2,2',4'-trioxo-1',2',3',4'-tetrahydrospiro[indoline-3,5'-pyrano[2,3-d]pyrimidine]-6'-carboxylate
• 英文别名: Ethyl 7'-amino-5-chloro-2,2',4'-trioxo-1,1',2,2',3',4'-hexahydrospiro[3h-indole-3,5'-[5h]pyrano[2,3-d]pyrimidine]-6'-carboxylate；ethyl 7'-amino-5-chloro-2,2',4'-trioxospiro[1H-indole-3,5'-1H-pyrano[2,3-d]pyrimidine]-6'-carboxylate
• CAS: 1380401-50-2
• 化学式: C₁₇H₁₃ClN₄O₆
• 分子量: 404.766
• InChiKey: YDHSMWCITLKSEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  149
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  巴比妥酸 、 5-氯靛红 、 氰乙酸乙酯 以 甘油 为溶剂， 反应 2.17h， 以92%的产率得到ethyl 7'-amino-5-chloro-2,2',4'-trioxo-1',2',3',4'-tetrahydrospiro[indoline-3,5'-pyrano[2,3-d]pyrimidine]-6'-carboxylate
  参考文献：
  名称：

  Glycerol as a biodegradable and reusable promoting medium for the catalyst-free one-pot three component synthesis of 4H-pyrans

  摘要：

  甘油作为绿色、生物可降解且可重复利用的促进介质，在无催化剂条件下用于一锅法三组分合成4H-吡喃。广泛的一系列底物，包括芳香和杂环醛、吲哚醌衍生物、苊醌和九氢吲哚，与具有活性α-亚甲基的羰基化合物及烷基丙二酸酯进行缩合反应。所有反应均在短时间内完成，产物收率良好至优异。反应介质可回收并重复使用多次，效率无任何损失。

  DOI：

  10.1039/c2gc35135h

文献信息

• A simple and clean method for multicomponent synthesis of spiro [indole-tetrahydropyrano(2,3-d)pyrimidine] derivatives using SBA-Pr-SO3H as catalyst under solvent-free conditions
  作者：Ghodsi Mohammadi Ziarani、Sakineh Faramarzi、Negar Lashgari、Alireza Badiei

  DOI：10.1007/s13738-013-0342-1

  日期：2014.6

  functionalized SBA-15 (SBA-Pr-SO3H) as a new nanoporous solid acid catalyst was applied in the green one-pot synthesis of spiro[indole-tetrahydropyrano(2,3-d)pyrimidine] derivatives via three-component reaction of isatins, malononitrile or cyanoacetic esters and barbituric acids under solvent-free conditions. SBA-Pr-SO3H was proved to be an efficient heterogeneous nanoporous solid acid catalyst with a pore

  磺酸功能化的SBA-15（SBA-Pr-SO 3 H）作为一种新型的纳米多孔固体酸催化剂，通过三步法一锅法合成绿色的一锅[[吲哚-四氢吡喃（2,3- d）嘧啶]衍生物]。染料，丙二腈或氰基乙酸酯与巴比妥酸在无溶剂条件下的组分反应。SBA-Pr-SO 3 H被证明是孔径为6 nm的高效多相纳米多孔固体酸催化剂，可通过简单过滤轻松处理并从反应混合物中除去，并且无需任何回收即可重复使用多次活动丧失。这种方法的优点是产品产量高，对环境无害，反应时间短，易于处理。
• Monoclinic zirconia nanoparticle-catalyzed regioselective synthesis of some novel substituted spirooxindoles through one-pot multicomponent reaction in a ball mill: A step toward green and sustainable chemistry
  作者：Shivam Bajpai、Sundaram Singh、Vandana Srivastava

  DOI：10.1080/00397911.2017.1336244

  日期：2017.8.18

  ABSTRACT A highly efficient, green as well as atom economical protocol for the synthesis of substituted spirooxindoles from m-ZrO2 NPs catalyzed multicomponent reaction of isatin derivatives with ethyl cyanoacetate and 1,3-dicarbonyl compounds in a ball mill has been established. Because of the simple and readily available starting materials, easy operation, and high bioactivity of substituted spirooxindoles

  摘要 建立了一种高效、绿色且原子经济的方案，用于从 m-ZrO2 NPs 催化靛红衍生物与氰乙酸乙酯和 1,3-二羰基化合物在球磨机中的多组分反应合成取代的螺吲哚。由于取代螺环吲哚的起始原料简单易得、操作方便、生物活性高，该策略可广泛应用于药物化学。m-ZrO2 Nps 催化剂的可回收性是所提出方法的另一个重点。图形概要
• An efficient, room temperature, oxygen radical anion (O₂^•−) mediated, one-pot, and multicomponent synthesis of spirooxindoles
  作者：Somaiah Gajaganti、Shivam Bajpai、Vandana Srivastava、Sundaram Singh

  DOI：10.1139/cjc-2017-0432

  日期：2017.12

  The present report highlights an efficient use of oxygen radical anion to promote a room temperature multi-component synthesis of spirooxindoles (4a–4l) under mild reaction conditions. The potassium superoxide (KO₂) and tetraethylammonium bromide (TEAB) combination generate the oxygen radical anion in situ to promote this transformation. This method offers a sustainable and direct access to the biologically important spirooxindole derivatives in good to excellent yields.

  该报告强调了高效利用氧自由基阴离子促进在温和反应条件下合成螺环氧吲哚（4a-4l）的多组分合成。钾超氧化物（KO₂）和溴化四乙铵（TEAB）的组合在原位产生氧自由基阴离子以促进这一转化。该方法提供了一种可持续且直接访问生物学上重要的螺环氧吲哚衍生物的途径，收率良好至优异。
• A new silica-supported organocatalyst based on L-proline: An efficient heterogeneous catalyst for one-pot synthesis of spiroindolones in water
  作者：Ali Khalafi-Nezhad、Elham Shaikhi Shahidzadeh、Samira Sarikhani、Farhad Panahi

  DOI：10.1016/j.molcata.2013.07.009

  日期：2013.11

  A simple and practical synthetic strategy for the synthesis of a novel silica-supported organocatalyst system based on L-proline (SSLP) has been developed. First, silica was treated with trimethoxy(vinyl)silane to produced a vinyl-silica (VS) substrate. Then, VS was oxidized using H2O2 to generate the silica-oxiran (SO) material. Finally, ring-opening of oxiranes in SO substrate with L-proline was resulted the production of SSLP catalyst. The catalytic performance of SSLP was evaluated in the three-component synthesis of spirooxindole derivatives via the condensation reaction of isatins and dicarbonyl compounds in water. All reactions were completed in short times and all products were obtained in good to excellent yields. Besides, SSLP could be recovered for 8 times without any additional treatments. (C) 2013 Elsevier B.V. All rights reserved.
• Glycerol as a biodegradable and reusable promoting medium for the catalyst-free one-pot three component synthesis of 4H-pyrans
  作者：Hamid Reza Safaei、Mohsen Shekouhy、Sudabeh Rahmanpur、Athar Shirinfeshan

  DOI：10.1039/c2gc35135h

  日期：——

  Glycerol is applied as a green, biodegradable and reusable promoting medium for one-pot three component synthesis of 4H-pyrans under catalyst-free conditions. A broad range of substrates including aromatic and heteroaromatic aldehydes, isatine derivatives, acenaphthenequinone and ninehydrine are condensed with carbonyl compounds possessing a reactive α-methylene group and alkylmalonates. All reactions are completed in short times, and the products are obtained in good to excellent yields. The reaction medium could be recycled and reused several times without any loss of efficiency.

  甘油作为绿色、生物可降解且可重复利用的促进介质，在无催化剂条件下用于一锅法三组分合成4H-吡喃。广泛的一系列底物，包括芳香和杂环醛、吲哚醌衍生物、苊醌和九氢吲哚，与具有活性α-亚甲基的羰基化合物及烷基丙二酸酯进行缩合反应。所有反应均在短时间内完成，产物收率良好至优异。反应介质可回收并重复使用多次，效率无任何损失。