2-(4-甲氧基苯基)咪唑并[1,2-a]吡啶-3-胺 | 80493-71-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-(4-甲氧基苯基)咪唑并[1,2-a]吡啶-3-胺
• 中文别名: 2-(4-甲氧基苯基)咪唑并[1,2-A]吡啶-3-胺
• 英文名称: 2-(4-methoxyphenyl)imidazo[1,2-a]pyridin-3-amine
• CAS: 80493-71-6
• 化学式: C₁₄H₁₃N₃O
• mdl: MFCD02658344
• 分子量: 239.277
• InChiKey: ITUOXVCQWLKCGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  52.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(tert-butyl)-2-(4-methoxyphenyl)imidazo[1,2-a]pyridin-3-amine 在 4-甲氧基苯甲醛 、 三氟乙酸 作用下， 以 1,2-二氯乙烷 为溶剂， 以69%的产率得到2-(4-甲氧基苯基)咪唑并[1,2-a]吡啶-3-胺
  参考文献：
  名称：

  Skeletal Diverse Synthesis of N-Fused Polycyclic Heterocycles via the Sequence of Ugi-Type MCR and CuI-Catalyzed Coupling/Tandem Pictet–Spengler Reaction

  摘要：

  Several diversity-oriented syntheses of N-fused polycyclic heterocycles have been demonstrated but most of them are based on point diversity within the same library and usually involve time-consuming sequential multistep syntheses, which also suffer from low yields and/or poor precursor scopes. We have developed a new strategy for the syntheses of skeletal diverse N-fused polycyclic compounds via an Ugi-type MCR followed by a CuI-catalyzed coupling reaction or tandem Pictet-Spengler reaction. This two-step sequence provides eight distinct skeleton of fused {6-5-5-6}, {5-5-5-6}, {6-5-6-6}, and {5-5-6-6} ring systems that have applications in medicinal chemistry and chemical genetics too.

  DOI：

  10.1021/jo202255v

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）。
• Electrochemical primary amination of imidazopyridines with azidotrimethylsilane under mild conditions
  作者：Yan Zhu、Qiao Chu、Heng Li、Ping Liu、Peipei Sun

  DOI：10.1039/d2gc03703c

  日期：——

  A straightforward protocol involved electrochemical primary amination of imidazopyridines under mild conditions was described, in which TMSN₃ was used as the nitrogen source and a trace amount of H₂O was used as the hydrogen source.

  描述了一种简单的协议，涉及在温和条件下电化学原位氨基化咪唑吡啶，其中使用TMSN3作为氮源，微量的H2O作为氢源。
• The full spectrum tuning of fluorescent molecules via a one-pot multicomponent reaction
  作者：Nathan Bedard、Addison G. Coen、Scott Pekarske、Andrew Sennett、Garrett J. Davis、Timothy Chavez、Dennis L. Lichtenberger、Christopher Hulme

  DOI：10.1016/j.tetlet.2023.154748

  日期：2023.10

  of tuning these fluorescent molecules to higher wavelengths. This is vital since different tissues are sensitive to varying wavelength emissions. To address this need, we report the discovery, tuning, structure-photophysical property relationships (SPPR), and time-dependent DFT (TD-DFT) computations of 400–700+ nm fluorescent pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolines and substituted imidazo[1,2-a]pyridin-3-amines

  用于成像的荧光探针能够对难以触及的细胞和细胞器进行可视化和分析。然而，将这些荧光分子调谐到更高波长的有效示例有限。这一点至关重要，因为不同的组织对不同波长的发射很敏感。为了满足这一需求，我们报道了 400–700+ nm 荧光吡啶[2′，1′：2,3]咪唑[4,5-c]异喹啉和取代的咪唑[1,2-a]吡啶-3-胺的发现、调谐、结构-光物理性质关系 （SPPR） 和时间依赖性 DFT （TD-DFT） 计算。合成涉及三甲基硅烷基氰化物 （TMSCN） 修饰的 Groebke-Blackburn-Bienaymé （GBB） 多组分反应以及 TMSCN 修饰的 GBB 结合随后的醛缩合，以及 Aza-Friedel-Crafts-分子内环化-氧化都在一个锅中。SPPR 揭示了氨基吡啶起始材料对位的吸电子强度直接控制这些分子的吸收和荧光发射波长。TD-DFT 计算显示了自然跃迁轨道 （NTO）
• Astik, R. R.; Thaker, K. A., Journal of the Indian Chemical Society, 1981, vol. 58, p. 1013 - 1014
  作者：Astik, R. R.、Thaker, K. A.

  DOI：——

  日期：——
• A novel dealkylation affording 3-aminoimidazo[1,2-a]pyridines: access to new substitution patterns by solid-phase synthesis
  作者：Christopher Blackburn、Bing Guan

  DOI：10.1016/s0040-4039(00)00003-4

  日期：2000.3

  The three-component synthesis of 5-aminoimidazo[1,2-a]pyridine derivatives has been extended by a novel acid-induced dealkyation reaction that removes the 1,1,3,3-tetramethylbutyl group derived from the isonitrile input. This reaction was conducted on the solid-phase using the HMBA linker and the resulting products subjected to reductive alkylation using several aldehydes, thereby accessing novel substitution patterns at the 3-position. (C) 2000 Elsevier Science Ltd.. All rights reserved.