3-(furan-2-yl)imidazo[1,5-a]pyridine | 325474-04-2

• 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: 3-(furan-2-yl)imidazo[1,5-a]pyridine
• CAS: 325474-04-2
• 化学式: C₁₁H₈N₂O
• mdl: MFCD01972336
• 分子量: 184.197
• InChiKey: LGLGYGAFVWTIAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 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：
  30.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(furan-2-yl)imidazo[1,5-a]pyridine 在 四(三苯基膦)钯 、 1,3-二碘-5,5-二甲基海因 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 水 为溶剂， 反应 13.0h， 生成
  参考文献：
  名称：

  Development of 1-aryl-3-furanyl/thienyl-imidazopyridine templates for inhibitors against hypoxia inducible factor (HIF)-1 transcriptional activity

  摘要：

  1,3-Disubstituted-imidazopyridines were designed for developing inhibitors against HIF-1 transcriptional activity. Designed compounds were rapidly synthesized from a key aromatic scaffold via microwave-assisted Suzuki-Miyaura coupling/C-H direct arylation sequence. Evaluation of ability to inhibit the hypoxia induced transcriptional activity of HIF-1 revealed that the compound 2i and 3a retained the same level of the inhibitory activity comparing with that of known inhibitor, YC-1 (1). Identified, readily accessible 1-aryl-3-furanyl/thienyl-imidazopyridine templates should be useful for future drug development. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.11.009
• 作为产物：
  描述：

  2-氨甲基吡啶 在 吡啶 、 碘 、 sulfur 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.67h， 生成 3-(furan-2-yl)imidazo[1,5-a]pyridine
  参考文献：
  名称：

  Development of 1-aryl-3-furanyl/thienyl-imidazopyridine templates for inhibitors against hypoxia inducible factor (HIF)-1 transcriptional activity

  摘要：

  1,3-Disubstituted-imidazopyridines were designed for developing inhibitors against HIF-1 transcriptional activity. Designed compounds were rapidly synthesized from a key aromatic scaffold via microwave-assisted Suzuki-Miyaura coupling/C-H direct arylation sequence. Evaluation of ability to inhibit the hypoxia induced transcriptional activity of HIF-1 revealed that the compound 2i and 3a retained the same level of the inhibitory activity comparing with that of known inhibitor, YC-1 (1). Identified, readily accessible 1-aryl-3-furanyl/thienyl-imidazopyridine templates should be useful for future drug development. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.11.009

文献信息

• A one-pot synthesis of imidazo[1,5-a]pyridines
  作者：James M. Crawforth、Melissa Paoletti

  DOI：10.1016/j.tetlet.2009.06.061

  日期：2009.8

  A one-pot synthesis of imidazo[1,5-a]pyridines starting from a carboxylic acid and 2-methylaminopyridines allowing introduction of various substituents at the 1- and 3-positions is achieved using propane phosphoric acid anhydride in ethyl or n-butyl acetate at reflux.

  使用丙烷磷酸酐在乙基或正丁基中的一锅合成方法，是从羧酸和2-甲基氨基吡啶开始的咪唑并[1,5- a ]吡啶和2-甲基氨基吡啶，这些取代基允许在1-和3-位引入各种取代基。回流乙酸盐。
• Persulfate promoted regioselective C-1 thiocyanation of imidazo[1,5-<i>a</i>]pyridines under visible light irradiation in water
  作者：Pallavi Saha、Samarpita Das、Harish K. Indurthi、Rohit Kumar、Deepak K Sharma

  DOI：10.1039/d4nj00327f

  日期：2024.4.22

  approach has been explored for regioselective C-1 thiocyanation of imidazo[1,5-a]pyridines. Reproducibility of the proposed methodology in the presence of diverse electron-donating and electron-withdrawing groups on the C-3 aryl ring and different heteroaryl and alkyl substituents at the C-3 position of the imidazo[1,5-a]pyridine nucleus widened the substrate scope. The proposed protocol is further reproducible

  一种可见光介导、无光催化剂、过硫酸盐促进的方法已被探索用于咪唑并[1,5- a ]吡啶的区域选择性C-1硫氰化。在 C-3 芳环上存在不同的给电子基团和吸电子基团以及咪唑并[1,5- a ]吡啶核的 C-3 位上存在不同的杂芳基和烷基取代基的情况下，所提出的方法的重现性底物范围。所提出的方案对于多种咪唑杂环可进一步重现。进行对照实验以研究反应机理。
• Cu(I)-Catalyzed Transannulation of <i>N</i>-Heteroaryl Aldehydes or Ketones with Alkylamines via C(sp³)–H Amination
  作者：Mingyang Li、Ying Xie、Yong Ye、Yong Zou、Huanfeng Jiang、Wei Zeng

  DOI：10.1021/ol503165b

  日期：2014.12.5

  A copper(I)-catalyzed direct transannulation of N-heteroaryl aldehydes or ketones with alkylamines via C-sp(3)-H amination has been achieved using molecular oxygen as a sole oxidant. N-Heteroarenes are employed as the amine source. This transformation provides a rapid and concise access to multifunctional imidazo[1,5-a]pyridines.
• Development of 1-aryl-3-furanyl/thienyl-imidazopyridine templates for inhibitors against hypoxia inducible factor (HIF)-1 transcriptional activity
  作者：Shinichiro Fuse、Toshiaki Ohuchi、Yasunobu Asawa、Shinichi Sato、Hiroyuki Nakamura

  DOI：10.1016/j.bmcl.2016.11.009

  日期：2016.12

  1,3-Disubstituted-imidazopyridines were designed for developing inhibitors against HIF-1 transcriptional activity. Designed compounds were rapidly synthesized from a key aromatic scaffold via microwave-assisted Suzuki-Miyaura coupling/C-H direct arylation sequence. Evaluation of ability to inhibit the hypoxia induced transcriptional activity of HIF-1 revealed that the compound 2i and 3a retained the same level of the inhibitory activity comparing with that of known inhibitor, YC-1 (1). Identified, readily accessible 1-aryl-3-furanyl/thienyl-imidazopyridine templates should be useful for future drug development. (C) 2016 Elsevier Ltd. All rights reserved.