2-chloro-3-phenylimidazo[1,2-a]pyridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-chloro-3-phenylimidazo[1,2-a]pyridine
• 化学式: C₁₃H₉ClN₂
• 分子量: 228.681
• InChiKey: IWZDMHLXZRDLMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-chloro-3-phenylimidazo[1,2-a]pyridine 、 苯硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 2.0h， 以88%的产率得到2,3-diphenyl-1H-imidazo[1,2-a]pyridine
  参考文献：
  名称：

  胺与羧酸的无过渡金属串联氯环化反应：获得氯咪唑并[1,2-α]吡啶

  摘要：

  报道了2-氨基吡啶与脂肪族羧酸的有效的一锅且无过渡金属的氯环化级联。这种转化为2-氯或3-氯取代的咪唑并[1，2-α]吡啶提供了一种新颖的方法，具有广泛的底物范围。

  DOI：

  10.1021/acs.orglett.5b01868
• 作为产物：
  描述：

  2-苯基-2-(2'-吡啶基氨基)-1,1,1-三氯乙烷 生成 2-chloro-3-phenylimidazo[1,2-a]pyridine
  参考文献：
  名称：

  BALON, YA. G.;SHULMAN, M. D.;SMIRNOV, V. A.;YUXOMENKO, M. M.;YUXOMENKO, M+, ZH. ORGAN. XIMII, 26,(1990) N, S. 1566-1571

  摘要：

  DOI：

文献信息

• A Cu(<scp>ii</scp>)-promoted tandem decarboxylative halogenation and oxidative diamination reaction of 2-aminopyridines with alkynoic acids for the synthesis of 2-haloimidazo[1,2-<i>a</i>]pyridines
  作者：Yun Liu、Wenhui Wang、Junwen Han、Jinwei Sun

  DOI：10.1039/c7ob02014g

  日期：——

  2-aminopyridines with alkynoic acids has been developed for the synthesis of 2-haloimidazo[1,2-a]pyridines. In this reaction, two C-N bonds and one C-halogen bond are formed in one pot, generating the desired products in good yields. This is the first report for the synthesis of 2- haloimidazo [1,2-a]pyridine derivatives from alkynoic acids.

  已经开发了铜促进的2-氨基吡啶与炔酸的级联脱羧卤化和氧化氨化反应顺序，用于合成2-卤代咪唑并[1,2-a]吡啶。在该反应中，在一个罐中形成两个CN键和一个C-卤素键，以高收率产生所需的产物。这是由炔酸合成2-卤代咪唑并[1,2-a]吡啶衍生物的第一份报告。
• Copper‐Promoted Annulation of Terminal Alkynes with 2‐Aminopyridines to Assemble 2‐Halogenated Imidazo[1,2‐ <i>a</i> ]pyridines
  作者：Yun Liu、Yuxuan Zhang、Jinwei Sun

  DOI：10.1002/jhet.3660

  日期：2019.10

  Copper‐promoted annulation reactions of terminal alkynes with 2‐aminopyridines have been developed for the synthesis of 2‐halogenated imidazo[1,2‐a]pyridines using copper halide as the halogen source. A variety of substrates survived under the reaction conditions and gave the desired products in good yields. This reaction features advantages such as easily available starting materials, broad substrate

  已开发了末端炔烃与2-氨基吡啶的铜促进环化反应，用于使用卤化铜作为卤素源来合成2-卤代咪唑并[1,2- a ]吡啶。在反应条件下，多种底物得以存活，并以良好的收率得到了所需的产物。该反应具有优点，例如容易获得的起始原料，广泛的底物范围和温和的反应条件。
• Copper-Catalyzed Intermolecular Oxidative Cyclization of Halo- alkynes: Synthesis of 2-Halo-substituted Imidazo[1,2-<i>a</i>]pyridines, Imidazo[1,2-<i>a</i>]pyrazines and Imidazo[1,2-<i>a</i>]pyrimidines
  作者：Yang Gao、Meizhou Yin、Wanqing Wu、Huawen Huang、Huanfeng Jiang

  DOI：10.1002/adsc.201300157

  日期：2013.8.12

  AbstractAn efficient copper‐catalyzed method for the synthesis of 2‐haloimidazopyridines with aminopyridines and haloalkynes using molecular oxygen as oxidant in a one‐pot manner has been developed. In this process, the reaction appears to be very general and suitable for the construction of a variety of 2‐halo‐substituted imidazopyridines, imidazopyrazines and imidazopyrimidines. The intermolecular oxidative diamination of haloalkynes was achieved for the first time. Importantly, the mild reaction conditions and the efficient conversion of the alkyl‐substituted haloalkynes are great improvements over the existing methods. Moreover, the resultant 2‐haloimidazo[1,2‐a]pyridines could be efficiently converted to other functionalized imidazopyridine products via substitution, coupling reactions and other transformations, which further indicates potential applications of this method in synthetic and pharmaceutical chemistry.magnified image
• BALON, YA. G.;SHULMAN, M. D.;SMIRNOV, V. A.;YUXOMENKO, M. M.;YUXOMENKO, M+, ZH. ORGAN. XIMII, 26,(1990) N, S. 1566-1571
  作者：BALON, YA. G.、SHULMAN, M. D.、SMIRNOV, V. A.、YUXOMENKO, M. M.、YUXOMENKO, M+

  DOI：——

  日期：——
• Transition-Metal-Free Tandem Chlorocyclization of Amines with Carboxylic Acids: Access to Chloroimidazo[1,2-α]pyridines
  作者：Xinsheng Xiao、Ying Xie、Siyi Bai、Yuanfu Deng、Huanfeng Jiang、Wei Zeng

  DOI：10.1021/acs.orglett.5b01868

  日期：2015.8.21

  An efficient one-pot and transition-metal-free chlorocyclization cascade of 2-aminopyridines with aliphatic carboxylic acids is reported. This transformation provides a novel approach to 2-chloro- or 3-chloro-substituted imidazo[1, 2-α]pyridines with a broad range of substrate scopes.

  报道了2-氨基吡啶与脂肪族羧酸的有效的一锅且无过渡金属的氯环化级联。这种转化为2-氯或3-氯取代的咪唑并[1，2-α]吡啶提供了一种新颖的方法，具有广泛的底物范围。