4-iodo-1-methoxy-3-p-tolyl-1H-pyrano[4,3-b]quinoline | 1256286-01-7

• 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: 4-iodo-1-methoxy-3-p-tolyl-1H-pyrano[4,3-b]quinoline
• 英文别名: 4-iodo-1-methoxy-3-phenyl-1H-pyrano[4,3-b]quinoline；4-iodo-1-methoxy-3-(4-methylphenyl)-1H-pyrano[4,3-b]quinoline
• CAS: 1256286-01-7
• 化学式: C₂₀H₁₆INO₂
• 分子量: 429.257
• InChiKey: FTBHVRITQCIPBC-UHFFFAOYSA-N

物化性质

• 熔点：
  110-112 °C
• 沸点：
  543.9±50.0 °C(predicted)
• 密度：
  1.62±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-iodo-1-methoxy-3-p-tolyl-1H-pyrano[4,3-b]quinoline 在 bis-triphenylphosphine-palladium(II) chloride 、 碘 、 potassium carbonate 、 二异丙胺 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 2-(4-methoxyphenyl)-3-(4-methylbenzoyl)-1-phenylpyrrolo[1,2-a]quinoline-4-carbaldehyde
  参考文献：
  名称：

  站点选择性亲电环化和随后的开环：到吡咯并[1,2- a ]喹啉和吲哚嗪的合成路线。

  摘要：

  描述了一种通过位点选择性亲电环化从吡喃并喹啉合成吡咯并[1,2- a ]喹啉和吲哚嗪的有效策略，随后在温和的反应条件下使用银/碘打开吡喃环。这种方法涉及的吡啶基的氮的优先攻击过的芳环，并导致5-地层内切-挖环化产物。C–N（ΔE a = 9.01 kcal / mol）和C–C（ΔE a为了使观察到的位点选择性合理化，进行＝ 31.31kcal / mol）的键形成。通过X射线晶体学研究证实了产物的结构。通过Pd催化的交叉偶联反应，通过亲电碘化反应生成的碘取代的化合物进一步多样化。

  DOI：

  10.1021/jo3015374
• 作为产物：
  描述：

  2-氯-3-喹啉甲醛 在 trans-bis(triphenylphosphine)palladium dichloride 、 碘 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 4-iodo-1-methoxy-3-p-tolyl-1H-pyrano[4,3-b]quinoline
  参考文献：
  名称：

  Pyrano[4,3-b]quinolines Library Generation via Iodocyclization and Palladium-Catalyzed Coupling Reactions

  摘要：

  Synthesis of a 80-member library of novel pyrano[4,3-b]quinoline in solution-Phase is reported. The key intermediate, 4-iodopyrano[4,3-b]quinolines were synthesized by the electropHic iodocyclization of corresponding oho-alkynyl ' aldehydes in good to excellent yields under mild reaction,conditions. Subsequently a diverse set of libraries was generated by employing palladium:catalyzed Suzuki-Miyauta, Heck, and Sonogashira coupling reactions on 4-iodopyrano[4,3-b]quinolines. In this:way,- a series of structurally different and biologically interesting molecules were obtained. Some of the selected compounds were screened against 3D7 strains of Plasmodium falciparum for antimalarial activity. Suzuki coupling products 6{3} and 6{21} and Heck coupling product 8{12} exhibit promising antimalarial activity.

  DOI：

  10.1021/co200100z

文献信息

• 2-(1-Benzotriazolyl)pyridine: A Robust Bidentate Ligand for the Palladium-Catalyzed CC (Suzuki, Heck, Fujiwara-Moritani, Sonogashira), CN and CS Coupling Reactions
  作者：Akhilesh K. Verma、Rajeev R. Jha、Ritu Chaudhary、Rakesh K. Tiwari、Abhinandan K. Danodia

  DOI：10.1002/adsc.201200583

  日期：2013.2.1

  designed and employed for the palladium-catalyzed CC (Suzuki, Heck, Fujiwara–Moritani, and Sonogashira), CN and CS coupling reactions. The ligand was found to be inexpensive, thermally stable, easy to synthesize from easily accessible starting materials on a multigram scale, show simplicity in use, and robustness in application, making this ligand effective for different coupling reactions. Suitably, the

  设计了一种新型的双齿配体1-（吡啶-2-基）-1 H-苯并[ d ] [1,2,3]三唑，并用于钯催化的CC（Suzuki，Heck，Fujiwara– Moritani和Sonogashira），CN和CS偶联反应。发现该配体便宜，热稳定，易于以几克规模由容易获得的起始原料合成，显示出使用简单性和在应用中的坚固性，从而使该配体对于不同的偶联反应有效。适当地，苯并三唑环的NN键的供体能力和吡啶环的N上的孤对电子增强了配体的二齿能力。
• Palladium-Catalyzed Regioselective [3 + 2] Annulation of Internal Alkynes and Iodo-pyranoquinolines with Concomitant Ring Opening
  作者：Trapti Aggarwal、Rajeev R. Jha、Rakesh K. Tiwari、Sonu Kumar、Siva K. Reddy Kotla、Sushil Kumar、Akhilesh K. Verma

  DOI：10.1021/ol3022935

  日期：2012.10.19

  A regioselective tandem synthesis of highly functionalized pyrrolo[1,2-a]quinolines has been developed through a novel strategy by palladium-catalyzed [3 + 2] annulation of iodo-pyranoquinolines and internal alkynes with subsequent ring opening. Pyranoquinoline with n-alkyl substitution at the 3-position leads to the formation of pyrrolo-acridones via [3 + 2] annulations/ring opening and successive

  通过钯催化的[3 + 2]碘-吡喃喹啉和内部炔烃的开环反应，通过新颖的策略开发了高度官能化的吡咯并[1,2- a ]喹啉的区域选择性串联合成。在3位上有正烷基取代的吡喃喹啉通过[3 + 2]环空/开环和连续的分子内跨羟醛缩合反应导致吡咯烷-rid啶酮的形成。
• Iodine-Mediated Solvent-Controlled Selective Electrophilic Cyclization and Oxidative Esterification of <i>o</i>-Alkynyl Aldehydes: An Easy Access to Pyranoquinolines, Pyranoquinolinones, and Isocumarins
  作者：Akhilesh K. Verma、Vineeta Rustagi、Trapti Aggarwal、Amit P. Singh

  DOI：10.1021/jo101526b

  日期：2010.11.19

  provides pyrano[4,3-b]quinolines 4a−f, via formation of cyclic iodonium intermediate Q; however, using alcohols as a solvent as well as nucleophile, o-alkynyl esters 5a−y were obtained selectively in good to excellent yields via formation of hypoiodide intermediate R. Subsequently, o-alkynyl esters were converted in to pyranoquinolinones 6a−i and isocoumarin 6j by electrophilic iodocyclization. This

  描述了碘在邻炔基醛的亲电碘环化中在不同溶剂中的化学选择性行为。与CH 2 Cl 2中的I 2与适当的亲核试剂反应生成邻炔基醛3a - t可以通过形成环碘鎓中间体Q生成吡喃并[4,3- b ]喹啉4a - f；但是，使用醇和亲核试剂作为溶剂，通过形成次碘化物中间体，选择性地以良好或优异的收率获得了邻炔基酯5a - y。[R 。随后，通过亲电碘环化将邻炔基酯转化为吡喃喹啉酮6a - i和异香豆素6j。这种发达的氧化酯化反应为从醛3n - p化学选择性合成酯5q - u而不氧化底物中存在的伯醇提供了新途径。
• Azidation vs [3 + 2]-cycloaddition: Chemoselective reaction of sodium azide towards o-alkynylaldehydes for the synthesis of N-heterocycles
  作者：Pradeep Kumar、Vineeta Garg、Akhilesh K. Verma

  DOI：10.1016/j.tetlet.2019.06.022

  日期：2019.7

  The chemoselective synthesis of functionalized azido- and triazolo-containing nitrogen heterocycles using sodium azide and o-alkynylaldehydes has been described. The azidation reaction was preferred in acetonitrile while the [3 + 2]-cycloaddition was favored in DMSO. Furthermore, the azido-pyranoquinolines were employed for the synthesis of benzonaphthyridines via the Staudinger reaction at room temperature

  已经描述了使用叠氮化钠和邻炔基醛化学合成官能化的含叠氮基和三唑基的氮杂环。在乙腈中优选叠氮化反应，而在DMSO中偏向[3 + 2]-环加成反应。此外，在室温下，通过Staudinger反应，将叠氮基-吡喃喹啉用于苯并萘并吡啶类化合物的合成。