N-(quinolin-5-yl)picolinamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-(quinolin-5-yl)picolinamide
• 英文别名: N-quinolin-5-ylpyridine-2-carboxamide
• 化学式: C₁₅H₁₁N₃O
• 分子量: 249.272
• InChiKey: GRMMOJZVZWMCNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  吗啉-4-基苯甲酸酯 、 N-(quinolin-5-yl)picolinamide 在 copper(II) acetate monohydrate 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 以79%的产率得到N-(6-morpholinoquinolin-5-yl)picolinamide
  参考文献：
  名称：

  Copper-Catalyzed Electrophilic Ortho C(sp²)–H Amination of Aryl Amines: Dramatic Reactivity of Bicyclic System

  摘要：

  A practical copper-catalyzed, 2-picolinamide-directed ortho C-H amination of anilines with benzoyl-protected hydroxylamines has been disclosed that proceeds smoothly without any external stoichiometric oxidant or additives. Remarkably, besides anilines, bicyclic naphthyl or heterocyclic amines furnished amination products with five- and six-membered cyclic and acyclic amines at the ortho position selectively. This electrophilic C-H amination also proceeds smoothly in water under slightly modified reaction conditions.

  DOI：

  10.1021/acs.orglett.9b01546
• 作为产物：
  描述：

  2-吡啶甲酸 在 4-二甲氨基吡啶 、 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 N-(quinolin-5-yl)picolinamide
  参考文献：
  名称：

  Copper-Catalyzed Electrophilic Ortho C(sp²)–H Amination of Aryl Amines: Dramatic Reactivity of Bicyclic System

  摘要：

  A practical copper-catalyzed, 2-picolinamide-directed ortho C-H amination of anilines with benzoyl-protected hydroxylamines has been disclosed that proceeds smoothly without any external stoichiometric oxidant or additives. Remarkably, besides anilines, bicyclic naphthyl or heterocyclic amines furnished amination products with five- and six-membered cyclic and acyclic amines at the ortho position selectively. This electrophilic C-H amination also proceeds smoothly in water under slightly modified reaction conditions.

  DOI：

  10.1021/acs.orglett.9b01546

文献信息

• Copper‐Catalyzed C‐4 Carboxylation of 1‐Naphthylamide Derivatives with CBr ₄ /MeOH
  作者：Tapan Sahoo、Chiranjit Sen、Harshvardhan Singh、E. Suresh、Subhash Chandra Ghosh

  DOI：10.1002/adsc.201900482

  日期：2019.9.3

  A simple and practical copper catalyzed C‐4 carboxylation reaction of 1‐naphthylamide derivatives using carbon tetra bromide and methanol is reported here. Picolinamide and its derivatives are used as a bidentate directing group for the distal C4‐H functionalization. Various substituted naphthylamide derivatives, and anilides are employed for the carboxylation and proceeds in good yields under mild

  本文报道了使用四溴化碳和甲醇进行简单而实用的铜催化的1-萘酰胺衍生物的C-4羧化反应。Picolinamide及其衍生物用作远端C4-H功能化的双齿引导基团。各种取代的萘酰胺衍生物和苯甲酸酯被用于羧化反应，并在温和的条件下以高收率进行。从实验结果可以看出，1-萘甲酰胺的C4-H羧化反应可能通过单电子转移（SET）途径进行。
• Heterogeneous copper-catalyzed C S coupling via insertion of sulfur dioxide: A novel and regioselective approach for the synthesis of sulfur-containing compounds
  作者：Junfen Han、Kai Wang、Guirong You、Guodong Wang、Jian Sun、Guiyun Duan、Chengcai Xia

  DOI：10.1016/j.catcom.2019.105708

  日期：2019.8

  A novel and regioselective protocol for CS coupling of naphthylamines via the insertion of sulfur dioxide was developed by employing a heterogeneous copper catalyst, providing desired products in moderate to good yields. This strategy gives a powerful tool for the efficient preparation of sulfur-containing compounds. Control experiments declared that a single-electron transfer mechanism (SET) is responsible

  通过使用多相铜催化剂，开发了一种新颖的区域选择性方案，用于通过插入二氧化硫使萘胺进行C S偶联，从而以中等至良好的收率提供了所需的产物。该策略为有效制备含硫化合物提供了强大的工具。对照实验表明，单电子转移机制（SET）负责该C S交叉偶联反应。
• Iron-Catalyzed Directed C(sp²)–H and C(sp³)–H Functionalization with Trimethylaluminum
  作者：Rui Shang、Laurean Ilies、Eiichi Nakamura

  DOI：10.1021/jacs.5b04818

  日期：2015.6.24

  Conversion of a C(sp(2))-H or C(sp(3))-H bond to the corresponding C-Me bond can be achieved by using AlMe3 or its air-stable diamine complex in the presence of catalytic amounts of an inorganic iron(III) salt and a diphosphine along with 2,3-dichlorobutane as a stoichiometric oxidant. The reaction is applicable to a variety of amide substrates bearing a picolinoyl or 8-aminoquinolyl directing group

  C(sp(2))-H 或 C(sp(3))-H 键转化为相应的 C-Me 键可以通过使用 AlMe3 或其空气稳定的二胺配合物在催化量的无机铁 (III) 盐和二膦以及作为化学计量氧化剂的 2,3-二氯丁烷。该反应适用于各种带有吡啶甲酰基或 8-氨基喹啉基导向基团的酰胺底物，能够使各种（杂）芳基、烯基和烷基酰胺甲基化。使用温和的铝试剂可防止铁发生不希望的还原，并允许反应以高达 6500 的催化剂周转数进行。
• Copper(II)-Mediated Chelation-Assisted Regioselective <i>N</i>-Naphthylation of Indoles, Pyrazoles and Pyrrole through Dehydrogenative Cross-Coupling
  作者：Sourav Pradhan、Pinaki Bhusan De、Tharmalingam Punniyamurthy

  DOI：10.1021/acs.joc.7b00615

  日期：2017.5.5

  picolinamide directed regioselective cross-coupling of naphthylamines with azoles is developed via C–H functionalization and C–N bond formation. The reaction of indoles leads to the formation of chiral C–N cross-coupled products with functional group tolerance. These reaction conditions can also be extended to the cross-coupling of pyrazole and pyrrole scaffolds.

  通过C–H官能化和C–N键的形成，开发了铜介导的吡啶啉对萘胺与吡咯的区域选择性交叉偶联。吲哚的反应导致形成具有官能团耐受性的手性C–N交叉偶联产物。这些反应条件也可以扩展到吡唑和吡咯支架的交叉偶联。
• Copper(II)-Catalyzed Direct Amination of 1-Naphthylamines at the C8 Site
  作者：Conghui Zu、Tingfang Zhang、Fan Yang、Yusheng Wu、Yangjie Wu

  DOI：10.1021/acs.joc.0c01672

  日期：2020.10.2

  A new and simple protocol for C8–H amination of 1-naphthylamine derivatives was developed using copper salt and di-tert-butyl peroxide (DTBP) as the catalyst and oxidant, respectively. This reaction proceeded smoothly under the additive and solvent-free conditions. In addition, this amination showed excellent regioselectivity and could tolerate various functional groups.

  分别使用铜盐和过氧化二叔丁基（DTBP）作为催化剂和氧化剂，开发了一种新的简单的1-萘胺衍生物C8-H氨基化方案。该反应在无添加剂和无溶剂的条件下顺利进行。另外，该胺化表现出优异的区域选择性并且可以耐受各种官能团。