3-(4-Chlorophenyl)-2-phenylimidazo[1,2-a]pyridine | 1414949-17-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4-Chlorophenyl)-2-phenylimidazo[1,2-a]pyridine
• CAS: 1414949-17-9
• 化学式: C₁₉H₁₃ClN₂
• 分子量: 304.779
• InChiKey: QSFNLPGYPCJQON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.32
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  N-[1-(4-chlorophenyl)-2-phenylethylidene]hydroxylamine 在 三氟甲磺酸 、 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 13.5h， 生成 3-(4-Chlorophenyl)-2-phenylimidazo[1,2-a]pyridine
  参考文献：
  名称：

  布朗斯台德酸催化 2-巯基吡啶和相关杂环对 2H-氮丙啶进行区域选择性开环；一锅法获得咪唑并[1,2-a]吡啶和咪唑并[2,1-b]噻唑

  摘要：

  开发了一种用于合成咪唑并[1,2- a ]吡啶的催化且通用的合成方法。布朗斯台德酸催化在 2 H-氮丙啶的区域选择性开环中起主要作用。通过巯基吡啶及其类似物的N中心进行亲核攻击，然后通过裂解 C-S 键进行环化，从而建立了咪唑并[1,2- a ]吡啶和相关杂环的文库。该反应方案已应用于各种 2 H-氮丙啶、2-巯基吡啶和噻唑-2-硫醇，说明了反应条件的通用性。实际应用包括药物的合成，例如抗肿瘤剂。这项研究介绍了一种合成具有广泛潜力的功能分子的新方法。

  DOI：

  10.1039/d4ob00410h

文献信息

• Metal-free C–H arylation of imidazoheterocycles with aryl hydrazines
  作者：Sourav Jana、Sadhanendu Samanta、Avik K. Bagdi、Valerii Z. Shirinian、Alakananda Hajra

  DOI：10.1039/c8ra01474d

  日期：——

  A simple and efficient metal-free arylation of imidazo[1,2-a]pyridines at the C-3 position with arylhydrazine has been achieved at room temperature under ambient air conditions. Various 2,3-disubstituted imidazopyridines and imidazothiazoles were synthesized with high yields. The present methodology demonstrates the usefulness of commercially available aryl hydrazine as an arylating agent.

  在室温和环境空气条件下，已经实现了在 C-3 位的咪唑并[1,2- a ]吡啶与芳基肼的简单有效的无金属芳基化。以高产率合成了各种 2,3-二取代的咪唑并吡啶和咪唑噻唑。本方法证明了可商购的芳基肼作为芳基化剂的有用性。
• An insight into the novel covalent functionalization of multi-wall carbon nanotubes with pseudopeptide backbones for palladium nanoparticles immobilization: A versatile catalyst towards diverse cross-coupling reactions in bio-based solvents
  作者：Ronak Afshari、Seyyed Emad Hooshmand、Mojtaba Atharnezhad、Ahmad Shaabani

  DOI：10.1016/j.poly.2019.114238

  日期：2020.1

  Abstract Materials functionalization with multicomponent reactions (MCRs) has grabbed a lot of attention nowadays due to the integration of outstanding features of MCRs with materials domains. Herein, we put the spotlight on the isocyanides and Meldrum’s acid-based MCRs route for the one-pot covalent functionalization of multi-wall carbon nanotubes (MWCNTs) which led to pseudopeptide-decorated MWCNTs

  摘要由于MCRs的杰出功能与材料领域的整合，具有多组分反应（MCR）的材料功能化如今引起了广泛的关注。在这里，我们将重点放在异氰酸酯和Meldrum的基于酸的MCR路线上，以实现多壁碳纳米管（MWCNT）的一锅共价功能化，这导致假肽修饰的MWCNT具有固定钯纳米颗粒的能力，并且可以用作现代催化系统。通过FT-IR，1 H NMR，XRD，SEM，TEM，EDX和TGA对合成的纳米催化剂进行表征。在生物基溶剂中检查了纳米催化剂对各种碳-碳交叉偶联反应的催化活性。结果表明，纳米催化剂对Csp2-Csp2的形成具有催化作用，Csp-Csp2和Csp-Csp通过均偶联和分子间Ullmann键，CH芳基化，Mizoroki-Heck，Sonogashira和GlaSEr偶联反应键合，在收率，反应时间，基于生物的介质和程序的化学选择性方面都有显着提高。此外，该方法通过保持多相催化剂的初始性能而没有任何
• Rhodium-Catalyzed Highly Regioselective C-H Arylation of Imidazo[1,2-a]pyridines with Aryl Halides and Triflates
  作者：Yi Liu、Lin He、Guoqiang Yin、Guojie Wu、Yingde Cui

  DOI：10.5012/bkcs.2013.34.8.2340

  日期：2013.8.20

  Accepted May 13, 2013A convenient Rh-catalyzed C-H arylation of imidazo[1,2-a]pyridines with a variety of aryl halides or triflateshas been reported. This process afforded a range of biaryl compounds in excellent yields and showed highactivity and broad scope. Key Words : Rhodium catalyst, Aryl halides, Regioselective arylation, Imidazo[1,2- a]pyridines, TriflatesIntroductionHeteroaromatics bearing aryl-heteroaryl

  E-mail: [e-mail] 2013年4月8日接收，2013年5月13日接受 已有报道一种方便的Rh催化CH芳基化咪唑并[1,2-a]吡啶与多种芳基卤化物或三氟甲磺酸酯。该方法以优异的收率提供了一系列联芳基化合物，并显示出高活性和广泛的适用范围。关键词：铑催化剂，芳基卤化物，区域选择性芳基化，咪唑并[1,2-a]吡啶，三氟甲磺酸盐简介带有芳基-杂芳基键的杂芳烃一直是生物化合物、天然产物、材料化学、配体中最重要的结构单元之一。
• Aerobic and Efficient Direct Arylation of Five-Membered Heteroarenes and Their Benzocondensed Derivatives with Aryl Bromides by Bulky α-Hydroxyimine Palladium Complexes
  作者：Bao-Tian Luo、Huan Liu、Zhi-Jie Lin、Jingxing Jiang、Dong-Sheng Shen、Rui-Zhi Liu、Zhuofeng Ke、Feng-Shou Liu

  DOI：10.1021/acs.organomet.5b00181

  日期：2015.10.26

  In the present work, a series of alpha-hydroxyimine palladium complexes with bulky substituents (i.e., [Ar-N=C(R)-C(R)(2)-OH]PdCl2} (C1, R = Me, Ar = 2-diphenylmethyl-4,6-dimethylphenyl; C2, R = Me, Ar = 2,6-bis(diphenylmethyl)-4-methylphenyl; C3, R = Me, Ar = 2,6-bis(diphenylinethyl)-4-methyoxylphenyl; C4, R = Me, Ar = 2,6-bis(diphenylmethyl)-4-chlorophenyl; C5, R = Ph, Ar = 2,6-dimethylphenyl; C6, R = Ph, Ar = 2,6-diisopropylphenyl)) were synthesized and characterized. The structures of palladium complexes C1 and C2 were determined by X-ray diffraction. These bidentate N,O-palladium complexes were applied for direct arylation under aerobic conditions. The effects of the reaction conditions and ligand substitution on the catalytic activity were evaluated. Upon a low palladium loading of 0.5 mol %, the bulky palladium complex C6 was successfully used to catalyze the cross-coupling of a variety of five-membered heteroarenes and their benzo-condensed derivatives with (hetero)aryl bromides. The mechanistic investigation on the direct arylation supported the involvement of a Pd(0)/Pd(II) CMD process.
• Highly regioselective palladium-catalyzed direct cross-coupling of imidazo[1,2-a]pyridines with arylboronic acids
  作者：Limin Zhao、Haiying Zhan、Jinqiang Liao、Jianping Huang、Qinlin Chen、Huifang Qiu、Hua Cao

  DOI：10.1016/j.catcom.2014.06.028

  日期：2014.11

  A highly regioselective method for the palladium-catalyzed direct cross-coupling of imidazo[1,2-a]pyridines with arylboronic acids has been developed by using O-2 as oxidant. This process can be applied to a wide range of imidazo[1,2-a]pyridines and arylboronic acids with excellent C-3-regioselectivity. It provides a new way for developing C-C bond-forming processes of multisubstituted imidazo[1,2-a]pyridines, which are common structural motifs in natural products and pharmaceuticals. (C) 2014 Elsevier B.V. All rights reserved.