3,5-Dimethyl-2-phenylimidazo<1,2-a>pyridine | 89193-03-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3,5-Dimethyl-2-phenylimidazo<1,2-a>pyridine
• 英文别名: 3,5-dimethyl-2-phenylimidazo[1,2-a]pyridine
• CAS: 89193-03-3
• 化学式: C₁₅H₁₄N₂
• mdl: MFCD25563839
• 分子量: 222.29
• InChiKey: MIFUVOUWZRCEOA-UHFFFAOYSA-N

物化性质

• 熔点：
  89-90 °C
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  17.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-氨基-6-甲基吡啶 、 苯,(2-硝基-1-丙烯基)-,(E)- 在 iron(II) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 以47%的产率得到3,5-Dimethyl-2-phenylimidazo<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。
• 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。
• The Directed Lithiation of 3-Methoxy-2-phenylimidazo[1,2-<i>a</i>]pyridine
  作者：Allen J. Guildford、Margaret A. Tometzki、Ralph W. Turner

  DOI：10.1055/s-1983-30593

  日期：——
• GUILDFORD, A. J.;TOMETZKI, M. A.;TURNER, R. W., SYNTHESIS, BRD, 1983, N 12, 987-989
  作者：GUILDFORD, A. J.、TOMETZKI, M. A.、TURNER, R. W.

  DOI：——

  日期：——
• Iron(II)-Catalyzed Denitration Reaction: Synthesis of 3-Methyl-2-arylimidazo[1,2-a]pyridine Derivatives from Aminopyridines and 2-Methylnitroolefins
  作者：Rulong Yan、Guosheng Huang、Hao Yan、Sizhuo Yang、Xiai Gao、Kang Zhou、Chao Ma

  DOI：10.1055/s-0032-1317685

  日期：——

  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.