2-(4-methoxyphenyl)imidazo[1,2-a]pyrimidin-3-amine | 89185-49-9

• 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-(4-methoxyphenyl)imidazo[1,2-a]pyrimidin-3-amine
• CAS: 89185-49-9
• 化学式: C₁₃H₁₂N₄O
• 分子量: 240.264
• InChiKey: RSJSRQQGXJRHAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  65.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(4-甲氧基苯基)-咪唑并[1,2-a]嘧啶 在 镍 氢气 、 sodium nitrite 作用下， 以 溶剂黄146 为溶剂， 生成 2-(4-methoxyphenyl)imidazo[1,2-a]pyrimidin-3-amine
  参考文献：
  名称：

  某些咪唑并[1,2-a]嘧啶衍生物的合成及抑菌活性。

  摘要：

  合成了75种咪唑并[1,2-a]嘧啶衍生物。据报道，这些化合物及其相应的α-溴代酮对多种革兰氏（+），革兰氏（-）细菌和分枝杆菌属物种具有“体外”抗菌活性。一些制备的衍生物表现出有效的抗微生物活性。

  DOI：

  10.1248/cpb.40.1170

文献信息

• Cyclisation reactions of some 3-nitrosoimidazo[1,2-a]-pyridines and-pyrimidines. Ring-opening/ring-closure reactions with triethyl phosphite: reassignment by X-ray crystal structure and nuclear magnetic resonance
  作者：Jean C. Teulade、Roger Escale、Henry Viols、Jean P. Chapat、Gérard Grassy、Alain Carpy、Jean M. Léger

  DOI：10.1039/p19830002663

  日期：——

  Deoxygenation of 3-nitroso-2-phenylimidazo[1,2-a]-pyridines and -pyrimidines with triethyl phosphite does not lead to the products described in the literature as pyrido- and pyrimido-imidazoindoles (3) and (4), but to the open-chain derivatives, N-(2-pyridyl)- and N-(2-pyrimidyl)-benzimidoyl cyanides (5) and (6). X-Ray crystallographic analysis confirms the structure of (5a): orthorhombic system with

  3-亚硝基-2-苯基咪唑并[1,2- a ]-吡啶和-嘧啶与亚磷酸三乙酯的脱氧作用不会导致文献中所述的产物为吡啶基和嘧啶基-咪唑并吲哚（3）和（4），但开链衍生物N-（2-吡啶基）-和N-（2-嘧啶基）-苯并亚甲基氰化物（5）和（6）。X射线晶体学分析证实了（5a）的结构：正交晶系，a = 24.377（6），b = 11.729（3），c = 7.534（2）Å，空间群Pbca，Z = 8，d = 1.27 g /厘米3，- [R= 0.061。用化合物（5）和（6）的亚磷酸三乙酯热闭环产生3-氨基-2-苯基咪唑并[1,2- a ]-吡啶和-嘧啶（8）和（9）。
• Ionic Liquid Promoted One-Pot Three-Component Reaction: Synthesis of Annulated Imidazo[1,2-a]azines Using Trimethylsilylcyanide
  作者：Ahmad Shaabani、Ali Maleki

  DOI：10.1007/s00706-006-0567-0

  日期：2007.1

  Imidazo[1,2- a ]azine derivatives are synthesized by a one-pot three-component reaction of an 2-aminoazine, an aldehyde, and trimethylsilylcyanide in the presence of 1- n -butyl-3-methylimidazolium bromide as a recoverable ionic liquid, in moderate to excellent yields with relatively short reaction times.

  咪唑并[1,2- a ]嗪衍生物是通过2-氨基嗪，醛和三甲基甲硅烷基氰化物在1 - n- 丁基-3-甲基咪唑鎓溴化物作为可回收离子存在下的一锅三组分反应合成的 液体，产率中等至优异，反应时间相对较短。
• Ultrasonic assisted synthesis of imidazo[1,2-a]azine catalyzed by ZnO nanorods
  作者：Samaheh Sadjadi、M. Eskandari

  DOI：10.1016/j.ultsonch.2012.09.006

  日期：2013.3

  ZnO nanorods have been successfully used as an efficient, economic, and reusable catalyst for the synthesis of imidazo[1,2-a]azine under ultrasonic irradiation. This procedure offers advantages in terms of higher yields, short reaction times and mild reaction conditions. (C) 2012 Elsevier B.V. All rights reserved.
• ZnO nanorods as an efficient catalyst for the synthesis of imidazo[1,2-a]azines and diazines
  作者：Samahe Sadjadi、Mehdi Eskandari

  DOI：10.1007/s00706-011-0655-7

  日期：2012.4

  ZnO nanorods were synthesized using a novel and solvent-free procedure and their catalytic activity in the preparation of imidazo[1,2-a]azines and diazines was studied. The effects of the amount of catalyst and its reusability were investigated to optimize the reaction conditions. The ZnO nanorods exhibited higher catalytic activity than that of bulk ZnO.
• Synthesis and Antibacterial Activity of Some Imidazo(1,2-a)pyrimidine Derivatives.
  作者：Yveline RIVAL、Gerard GRASSY、Georges MICHEL

  DOI：10.1248/cpb.40.1170

  日期：——

  A series of 75 imidazo[1,2-a]pyrimidine derivatives were synthesized. The "in vitro" antibacterial activity of these compounds and their corresponding alpha-bromoketones against a variety of gram (+), gram (-) bacteria and Mycobacterium species is reported. Some of the prepared derivatives exhibited potent antimicrobial activity.

  合成了75种咪唑并[1,2-a]嘧啶衍生物。据报道，这些化合物及其相应的α-溴代酮对多种革兰氏（+），革兰氏（-）细菌和分枝杆菌属物种具有“体外”抗菌活性。一些制备的衍生物表现出有效的抗微生物活性。