2-(furan-2-yl)-3-methylimidazo[1,2-a]pyridine | 28795-42-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 2-(furan-2-yl)-3-methylimidazo[1,2-a]pyridine
• CAS: 28795-42-8
• 化学式: C₁₂H₁₀N₂O
• 分子量: 198.224
• InChiKey: QJAZIFAXRWPSGP-UHFFFAOYSA-N

物化性质

• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  30.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氨基吡啶 、 (E)-2-(2-nitroprop-1-en-1-yl)furan 在 iron(II) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 以62%的产率得到2-(furan-2-yl)-3-methylimidazo[1,2-a]pyridine
  参考文献：
  名称：

  Iron(II)-Catalyzed Denitration Reaction: Synthesis of 3-Methyl-2-arylimidazo[1,2-a]pyridine Derivatives from Aminopyridines and 2-Methylnitroolefins

  摘要：

  A variety of ways to synthesize imidazo[1,2-a]pyridines have been reported and many approaches are devoted to the functionalization of imidazo[1,2-a]pyridines. However, the use of a denitration reaction in the synthesis of imidazo[1,2-a]pyridines has not been reported. We report here the iron-catalyzed synthesis of 3-methyl-2-arylimidazo [1,2-a] pyridine derivatives from aminopyridines and 2-methyl-nitroolefins. The procedure, using FeCl2 as catalyst, is simple and inexpensive. Various functional groups are tolerated and provide the products in good yields.

  DOI：

  10.1055/s-0032-1317685

文献信息

• Iron(III)-Catalyzed Denitration Reaction: One-Pot Three-Component Synthesis of Imidazo[1,2-<i>a</i>]pyridine Derivatives
  作者：Hao Yan、Yuling Wang、Congming Pan、Hao Zhang、Sizhuo Yang、Xiaoyu Ren、Jian Li、Guosheng Huang

  DOI：10.1002/ejoc.201301658

  日期：2014.5

  An iron(III)-catalyzed one-pot three-component cross-coupling nitration reaction of 2-aminopyridines, aldehydes and nitroalkanes, straightforwardly forms imidazo[1,2-a]pyridine derivatives and is described in this report. The system shows good functional-group tolerance and proceeds smoothly in moderate to good yields.

  铁 (III) 催化的 2-氨基吡啶、醛和硝基烷烃的一锅三组分交叉偶联硝化反应直接形成咪唑并 [1,2-a] 吡啶衍生物，并在本报告中进行了描述。该系统显示出良好的官能团耐受性，并以中等至良好的产率顺利进行。
• Copper-Catalyzed Decarboxylative Three-Component Reactions for the Synthesis of Imidazo[1,2-a]pyridines
  作者：Thiruvengadam Palani、Kyungho Park、Manian Rajesh Kumar、Hyun Ming Jung、Sunwoo Lee

  DOI：10.1002/ejoc.201200679

  日期：2012.9

  Imidazo[1,2-a]pyridine derivatives were synthesized through multicomponent coupling reactions of 2-aminopyridines, aldehydes, and alkynecarboxylic acids in the presence of 10 mol-% CuI/Cu(OTf)2. Both aryl- and alkyl-substituted alkynecarboxylic acids, including propiolic acid, were good alkyne sources and afforded the desired imidazo[1,2-a]pyridines in good yields through the decarboxylative coupling

  在 10 mol% CuI/Cu(OTf)2 存在下，通过 2-氨基吡啶、醛和炔羧酸的多组分偶联反应合成了咪唑并 [1,2-a] 吡啶衍生物。芳基和烷基取代的炔烃羧酸，包括丙炔酸，都是良好的炔烃来源，并通过脱羧偶联反应以良好的产率提供所需的咪唑并 [1,2-a] 吡啶。芳基炔羧酸是通过芳基碘化物和丙炔酸之间的钯催化偶联反应合成的，并与 2-氨基吡啶和醛反应，有或没有纯化步骤。在这两种情况下，都以良好的收率获得了所需的咪唑并[1,2-a]吡啶。机理研究表明，在丙炔酸的情况下，脱羧加成优于末端炔加成。
• One-Pot Synthesis of 3-Methyl-2-arylimidazo[1,2-<i>a</i>]pyridines Using Calcium Carbide as an Alkyne Source
  作者：Wei Chen、Zheng Li

  DOI：10.1021/acs.joc.1c01877

  日期：2022.1.7

  An efficient method for the construction of 3-methyl-2-arylimidazo[1,2-a]pyridines from the reactions of calcium carbide, 2-aminopyridines, and aromatic aldehydes is described. The notable advantages for this strategy include the use of an inexpensive and concise solid alkyne source, cheap and readily available raw materials, wide-scope substrates, and a simple work-up procedure.

  描述了一种由电石、2-氨基吡啶和芳香醛反应构建 3-甲基-2-芳基咪唑并[1,2- a ] 吡啶的有效方法。该策略的显着优势包括使用廉价且简洁的固体炔烃源、廉价且容易获得的原材料、广泛的底物和简单的后处理程序。
• Polyethylene Gylcol (PEG-400) as an Efficient and Recyclable Reaction Medium for One-Pot Three-Component Synthesis of Imidazo[1,2-a]pyridine Derivatives
  作者：P. Ramesh、K. Bhaskar

  DOI：10.14233/ajchem.2016.20061

  日期：——

  Polyethylene glycol (PEG) was found to be an inexpensive nontoxic and effective medium for the one-pot three-component synthesis of imidazo[1,2-a]pyridine derivatives under catalyst-free conditions in excellent yields. Environmental acceptability, low cost, high yields and recyclability of the polyethylene glycol are the important features of this protocol.

  研究发现，聚乙二醇（PEG）是一种廉价、无毒且有效的介质，可在无催化剂条件下单锅三组分合成咪唑并[1,2-a]吡啶衍生物，且收率极高。环境可接受性、低成本、高产率以及聚乙二醇的可回收性是该方案的重要特点。
• Synthesis and antimicrobic effect of furyl-substituted indolizine, imidazo[1,2-a]pyridine, and imidazo[2,1-b]thiazole
  作者：N. O. Saldabol、L. N. Alekseeva、B. A. Brizga、L. V. Kruzmetra、S. A. Giller

  DOI：10.1007/bf00771802

  日期：1970.7