6-溴-2-对甲苯基咪唑并[1,2-a]吡啶-3-羧醛 | 725253-27-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 6-溴-2-对甲苯基咪唑并[1,2-a]吡啶-3-羧醛
• 英文名称: 6-bromo-2-phenylimidazo[1,2-a]pyridine-3-carbaldehyde
• CAS: 725253-27-0
• 化学式: C₁₄H₉BrN₂O
• mdl: MFCD04117009
• 分子量: 301.142
• InChiKey: PNBBYIOMDIULGP-UHFFFAOYSA-N

物化性质

• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-溴-2-对甲苯基咪唑并[1,2-a]吡啶-3-羧醛 在 水 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 2-(6-bromo-2-phenylimidazo[1,2-a]pyridin-3-yl)-1-(pyrrolidin-1-yl)ethanone
  参考文献：
  名称：

  咪唑并吡啶和咪唑并噻唑的二溴代烯烃胺化反应的无金属方法制备唑吡坦，毒杀em及其类似物

  摘要：

  阐述了一种新的两步法制备唑吡坦，阿吡培南及其类似物。使用CBr 4 -PPh 3体系对相应的醛进行Wittig烯化反应，制得了一组由咪唑并吡啶和咪唑并噻唑衍生的未知二溴代烯烃。在水的存在下，用不同的伯胺和仲胺对二溴烯烃进行胺化可直接导致目标药物及其类似物的产率高达95％。

  DOI：

  10.1002/ejoc.201900279
• 作为产物：
  描述：

  2-氨基-5-溴吡啶 在 碳酸氢钠 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 3.5h， 生成 6-溴-2-对甲苯基咪唑并[1,2-a]吡啶-3-羧醛
  参考文献：
  名称：

  Metal-free oxidative decarbonylative halogenation of fused imidazoles

  摘要：

  已经开发出一种高效策略，用于在温度控制下，在TBHP存在的情况下对卡巴醛咪唑融合杂环进行脱甲酰卤代反应。

  DOI：

  10.1039/d1nj04440k

文献信息

• Copper-catalyzed intramolecular dehydrogenative cyclization: direct access to sensitive formyl-substituted imidazo[1,2-a]pyridines
  作者：Li-Hai Zhai、Li-Hong Guo、Bai-Wang Sun

  DOI：10.1039/c5ra19085a

  日期：——

  A direct method for the synthesis of formyl-substituted imidazo[1,2-a]pyridines was achieved easily from cyclization of aminopyridines and cinnamaldehydes via copper catalysis. This oxidative cyclization process involved direct C–H bond functionalization, and C–C/C–N bond formation. In this transformation, the sensitive aldehyde group was preserved under oxidative conditions.

  通过铜催化氨基吡啶和肉桂醛的环化，很容易实现直接合成甲酰基取代的咪唑并[1,2- a ]吡啶的直接方法。这种氧化环化过程涉及直接的C–H键功能化和C–C / C–N键形成。在该转化中，敏感的醛基在氧化条件下得以保留。
• Ru(II)-Catalyzed Synthesis of Fused Imidazo[1,2-<i>a</i>]pyridine-chromenones and Methylene-Tethered Bis-imidazo[1,2-<i>a</i>]pyridines and Regioselective O-Acetoxylation of Imidazo[1,2-<i>a</i>]pyridines
  作者：Javeed Ahmad Tali、Ravi Shankar

  DOI：10.1021/acs.orglett.3c00578

  日期：2023.5.12

  unprecedented protocol via ruthenium-catalyzed annulation for the synthesis of 6H-chromeno[4′,3′:4,5]imidazo[1,2-a]pyridin-6-one, and functionalized 2-(3-formylimidazo[1,2-a]pyridin-2-yl)phenyl acetate has been revealed by intramolecular chelation-assisted C–H activation. Additionally, a one-pot approach for creating bis(2-phenylimidazo[1,2-a]pyridin-3-yl)methane (BIP) has been realized through ruthenium

  在此，我们公开了一种前所未有的通过钌催化环化合成 6 H -chromeno[4',3':4,5]imidazo[1,2- a ]pyridin-6-one 和功能化 2-(已通过分子内螯合辅助的 C-H 活化揭示了3-甲酰咪唑并 [1,2- a ] 吡啶-2-基) 乙酸苯酯。此外，通过使用甲酸的钌催化，已经实现了用于产生双（2-苯基咪唑并[1,2- a ]吡啶-3-基）甲烷（BIP）的一锅法。该方法用于 BIP 的克级合成和已上市药物佐利米丁的经济步骤后期功能化，收率良好。
• K₂S₂O₈‐Mediated C‐3 Formylation of Imidazopyridines Using Glyoxylic Acid
  作者：Harish K. Indurthi、Samarpita Das、Pallavi Saha、Deepak K. Sharma

  DOI：10.1002/ejoc.202300829

  日期：2023.12

  A metal-free formylation of imidazopyridines with K2S2O8 by direct decarboxylative cross-coupling of glyoxylic acid is described. This reaction features broad substrate scope, good functional group tolerance, and generate products in good yields.

  描述了通过乙醛酸的直接脱羧交叉偶联用K 2 S 2 O 8进行咪唑并吡啶的无金属甲酰化。该反应底物范围广，官能团耐受性好，产物收率高。
• Facile synthesis of new imidazo[1,2-a]pyridines carrying 1,2,3-triazoles via click chemistry and their antiepileptic studies
  作者：Shrikanth Ulloora、Ramakrishna Shabaraya、Airody Vasudeva Adhikari

  DOI：10.1016/j.bmcl.2013.03.086

  日期：2013.6

  The present article reports the synthesis and anticonvulsant studies of new 2-arylimidazo[1,2-a]pyridines carrying suitably substituted 1,2,3-triazoles as well as their intermediates. The structures of newly synthesized compounds were confirmed by various spectroscopic techniques. The anticonvulsant study was carried out by MES and scPTZ screening methods, while their toxicity study was performed following Rotarod method. The active compounds showed enhanced seizure control in scPTZ method when compared with that of MES method. Compounds 3f, 4c, 4f, 5k, 5p and 5w carrying active pharmacophores exhibited complete protection against seizure and their results were comparable with standard drug diazepam. Majority of new compounds were found to be non-toxic, while few of them showed toxicity at 100 mg/kg. The c log P values of target compounds are in the range of 3.5-5.3, which confirm their lipophilic nature. (C) 2013 Elsevier Ltd. All rights reserved.
• Metal-free oxidative decarbonylative halogenation of fused imidazoles
  作者：Davinder Singh、Javeed Ahmad Tali、Gulshan Kumar、Ravi Shankar

  DOI：10.1039/d1nj04440k

  日期：——

  An efficient strategy has been developed for the deformylative halogenation of carbaldehyde imidazo-fused heterocycles in the presence of TBHP controlled by temperature.

  已经开发出一种高效策略，用于在温度控制下，在TBHP存在的情况下对卡巴醛咪唑融合杂环进行脱甲酰卤代反应。