ethyl 2-(4-methyl-phenyl)imidazo[1,2-a]pyridine-3-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 2-(4-methyl-phenyl)imidazo[1,2-a]pyridine-3-carboxylate
• 英文别名: ethyl 2-(p-tolyl)imidazo[1,2-a]pyridine-3-carboxylate；ethyl 2-(4-methylphenyl)imidazo[1,2-a]pyridine-3-carboxylate；2-p-Tolyl-imidazo[1,2-a]pyridine-3-carboxylic acid ethyl ester
• 化学式: C₁₇H₁₆N₂O₂
• 分子量: 280.326
• InChiKey: KFOYJIBAAAQONP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  C₁₇H₁₈N₂O₂ 在 copper(l) iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 ethyl 2-(4-methyl-phenyl)imidazo[1,2-a]pyridine-3-carboxylate
  参考文献：
  名称：

  Cu(I)-Catalysed Oxidative Coupling of 2-Aminopyridines with β-Keto Esters: Synthesis of Imidazo[1,2-a]Pyridine-3-Carboxylates

  摘要：

  以空气为氧化剂，铜催化 2-氨基吡啶与 β-酮酯的 C-N 直接氧化偶联，生成咪唑并[1,2-a]吡啶-3-羧酸盐，该方法简单、经济、环保。咪唑并[1,2-a]吡啶是多种生物和药理化合物的基本骨架。

  DOI：

  10.3184/174751912x13415906694258

文献信息

• Synthesis and Binding Affinity of 2-Phenylimidazo[1,2-<i>a</i>]pyridine Derivatives for both Central and Peripheral Benzodiazepine Receptors. A New Series of High-Affinity and Selective Ligands for the Peripheral Type
  作者：Giuseppe Trapani、Massimo Franco、Laura Ricciardi、Andrea Latrofa、Giuseppe Genchi、Enrico Sanna、Francesca Tuveri、Elisabetta Cagetti、Giovanni Biggio、Gaetano Liso

  DOI：10.1021/jm970112+

  日期：1997.9.1

  prepared following new synthetic methods, and their affinities for both the central (CBR) and the peripheral (PBR) benzodiazepine receptors evaluated. The compounds of the ester series displayed low affinity for both receptor types. Conversely, most of N,N-dialkyl(2-phenylimidazo[1,2-alpha]pyridin-3-yl)acetamides 7e-t proved to possess high affinity and selectivity for CBR or PBR depending on the nature

  若干个6-取代或6,8-二取代的2-苯基咪唑并[1,2-α-吡啶-3-羧酸烷基酯5a-h，-乙酸酯5i-s，6a-g和-丙酸酯5t，6h和N，N-二烷基-2-苯基咪唑并[1,2-α吡啶-3-甲酰胺7a-d，-乙酰胺7e-t或-丙酰胺7u是按照新的合成方法制备的，并且它们对两个环的亲和力（CBR ）和外围（PBR）苯并二氮杂receptor受体进行了评估。酯系列化合物对两种受体类型均显示出低亲和力。相反，大多数N，N-二烷基（2-苯基咪唑并[1,2-α吡啶基-3-基]乙酰胺）7e-t对CBR或PBR具有高亲和性和选择性，这取决于C（C 6）-和/或杂环系统上的C（8）。特别是，6-取代的化合物7f-n的IC50值之比（IC50（CBR）/ IC50（PBR））为0.32（7m）至232（7k），而6,8-二取代的化合物7o-t大于PBR的选择性是CBR的1000倍。检查了几种不同的苯二氮卓类
• Synthesis of Imidazopyridines via Copper-Catalyzed, Formal Aza-[3 + 2] Cycloaddition Reaction of Pyridine Derivatives with α-Diazo Oxime Ethers
  作者：Sangjune Park、Hyunseok Kim、Jeong-Yu Son、Kyusik Um、Sooho Lee、Yonghyeon Baek、Boram Seo、Phil Ho Lee

  DOI：10.1021/acs.joc.7b01714

  日期：2017.10.6

  The Cu-catalyzed, formal aza-[3 + 2] cycloaddition reaction of pyridine derivatives with α-diazo oxime ethers in trifluoroethanol was used to synthesize imidazopyridines via the release of molecular nitrogen and elimination of alcohol. These methods enabled modular synthesis of a wide range of N-heterobicyclic compounds such as imidazopyridazines, imidazopyrimidines, and imidazopyrazines with an α-imino

  吡啶衍生物与α-重氮肟醚在三氟乙醇中的Cu催化的正式aza- [3 + 2]环加成反应用于通过释放分子氮和消除醇来合成咪唑并吡啶。这些方法能够与由α-重氮肟醚和铜生成的α-亚氨基Cu-类胡萝卜素模块化合成多种N-杂环双环化合物，例如咪唑并哒嗪，咪唑并嘧啶和咪唑并吡嗪。
• Palladium-catalyzed regioselective direct C–H bond alkoxycarbonylation of 2-arylimidazo[1,2-<i>a</i>]pyridines
  作者：Arezoo Tanbakouchian、Ebrahim Kianmehr

  DOI：10.1039/d1nj00605c

  日期：——

  A palladium-catalyzed practical and efficient method to access alkoxycarbonylated imidazo[1,2-a]pyridines at the C-3 position has been developed based on the association of W(CO)6 as a safe and easy-to-handle CO surrogate and related alcohols. Through this synthetic strategy, a wide range of alkoxycarbonylated imidazo[1,2-a]pyridines with moderate to high yields have been prepared, which are important

  基于 W(CO) 6作为安全且易于处理的 CO 替代物的结合，开发了一种钯催化的实用且有效的方法来获取C-3 位的烷氧基羰基化咪唑并 [1,2- a ] 吡啶和相关的酒精。通过这种合成策略，已经制备了多种具有中等至高产率的烷氧基羰基化咪唑并[1,2- a ]吡啶，它们是医药产品中的重要结构基序。
• Imidazo[1,2-A]pyridine-3-carboxylate derivative and preparation method thereof
  申请人：KNU-INDUSTRY COOPERATION FOUNDATION

  公开号：US10323033B2

  公开（公告）日：2019-06-18

  Provided are an imidazo[1,2-a]pyridine-3-carboxylate derivative and a preparation method thereof, and more particularly, a method of effectively preparing an imidazo[1,2-a]pyridine-3-carboxylate derivative by performing an aza-[3+2] cycloaddition reaction of a pyridine derivative with an α-diazo oxime ether derivative in the presence of a copper (II) catalyst, and an imidazo[1,2-a]pyridine-3-carboxylate derivative prepared thereby.

  本发明提供了一种咪唑并[1,2-a]吡啶-3-羧酸盐衍生物及其制备方法，更具体地说，是一种通过吡啶衍生物与α-重氮肟发生偶氮-[3+2]环加成反应有效制备咪唑并[1、2-a]吡啶-3-羧酸盐衍生物的有效制备方法，该方法通过在铜（II）催化剂存在下进行吡啶衍生物与α-重氮肟醚衍生物的偶氮-[3+2]环加成反应，以及由此制备的咪唑并[1,2-a]吡啶-3-羧酸盐衍生物。
• IMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLATE DERIVATIVE AND PREPARATION METHOD THEREOF
  申请人：KNU-INDUSTRY COOPERATION FOUNDATION

  公开号：US20180354948A1

  公开（公告）日：2018-12-13

  Provided are an imidazo[1,2-a]pyridine-3-carboxylate derivative and a preparation method thereof, and more particularly, a method of effectively preparing an imidazo[1,2-a]pyridine-3-carboxylate derivative by performing an aza-[3+2] cycloaddition reaction of a pyridine derivative with an α-diazo oxime ether derivative in the presence of a copper (II) catalyst, and an imidazo[1,2-a]pyridine-3-carboxylate derivative prepared thereby.