2-amino-6-(2-oxo-2H-chromen-3-yl)-4-(3-nitrophenyl)nicotinonitrile | 1161101-43-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-amino-6-(2-oxo-2H-chromen-3-yl)-4-(3-nitrophenyl)nicotinonitrile
• 英文别名: 2-Amino-4-(3-nitrophenyl)-6-(2-oxochromen-3-yl)pyridine-3-carbonitrile
• CAS: 1161101-43-4
• 化学式: C₂₁H₁₂N₄O₄
• 分子量: 384.351
• InChiKey: MDSBYUJBIBCJNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  135
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  水杨醛 在 ammonium acetate 、 二甲胺 作用下， 以 水 为溶剂， 反应 1.0h， 生成 2-amino-6-(2-oxo-2H-chromen-3-yl)-4-(3-nitrophenyl)nicotinonitrile
  参考文献：
  名称：

  一种新型的可重复使用的离子标记纳米磁性催化剂：通过乙烯基异端基氧化制备2-氨基-6-（2-oxo-2 H -chromen-3-yl）-4-芳基烟腈的应用

  摘要：

  此，我们报告的Fe 3 ö 4 @O 2 PO 2（CH 2）2 NH 3 + CF 3 CO 2 -作为一种新型的和可重复使用的离子标记的纳米磁性催化剂。它的特征在于多种技术，包括傅立叶变换红外（FT-IR）光谱，热重分析/差热分析（​​TGA / DTA），扫描电子显微镜（SEM），透射电子显微镜（TEM），振动样品磁力计（VSM）和能量色散X射线（EDX）分析。Fe 3 O 4 @O 2 PO 2（CH2）2 NH 3 + CF 3 CO 2 -在合成2-氨基-6-（2-氧代-2-检查ħ -苯并吡喃-3-基）-4- arylnicotinonitrile衍生物。实验数据已经证实，该合理机理的最后一步是通过基于乙烯基异端基的氧化机理进行的。所描述的催化剂在所述的多组分反应中显示出极好的回收和再利用的潜力。

  DOI：

  10.1016/j.mcat.2018.11.009

文献信息

• A practical and highly efficient synthesis of densely functionalized nicotinonitrile derivatives catalyzed by zinc oxide-decorated superparamagnetic silica attached to graphene oxide nanocomposite
  作者：Farahnaz Davoodi、Mohammad G. Dekamin、Zahra Alirezvani

  DOI：10.1002/aoc.4735

  日期：2019.4

  porosity and magnetic properties. The catalytic activity of Fe3O4/SiO2/PTS‐GO‐ZnO, as a reusable heterogeneous catalyst, was investigated for efficient one‐pot multi‐component synthesis of medicinally important functionalized 2‐amino‐6‐(2‐oxo‐2H‐chromen‐3‐yl)‐4‐arylnicotinonitrile derivatives. The significant features of the present procedure are mild reaction conditions, low loading of the catalyst

  设计了一种以氧化锌修饰的超顺磁性氧化硅（Fe 3 O 4 / SiO 2 / PTS-GO-ZnO）作为新型纳米复合材料，并通过不同的光谱学或显微镜方法对其核壳结构进行了适当表征。热技术以及其孔隙率和磁性的测量。研究了Fe 3 O 4 / SiO 2 / PTS-GO-ZnO作为可重复使用的非均相催化剂的催化活性，以有效地一锅多组分合成医学上重要的官能化2-氨基-6-（2-氧代- 2小时-chromen-3-yl）-4-芳基烟腈衍生物。本方法的显着特征是温和的反应条件，催化剂的低负荷，所需产物的高至定量收率，避免使用有毒的重金属或溶剂，产物的简单分离和纯化以及稳定性以及至少连续运行六次后，催化剂可重复使用。
• An eco-friendly catalytic route for one-pot synthesis of 2-amino-6-(2-oxo-2Hchromen-3-yl)-4-arylnicotinonitrile derivatives by silica-supported perchloric acid (HClO4–SiO2) under solvent-free conditions
  作者：Majid Ghashang、Krishnamoorthy Aswin、Syed Sheik Mansoor

  DOI：10.1007/s11164-013-1027-1

  日期：2014.3

  A facile and environmentally benign synthesis of some 2-amino-6-(2-oxo-2H-chromen-3-yl)-4-arylnicotinonitrile derivatives from the reaction of 3-acetylcoumarin, aromatic aldehydes, and malononitrile under solvent-free condition in the presence of silica-supported perchloric acid (HClO4–SiO2) is described. The ability to reuse the catalyst, the high yields, and ease of purification are the important

  在无溶剂的情况下，由3-乙酰香豆素，芳香醛和丙二腈反应轻松合成一些2-氨基-6-（2-oxo-2 H -chromen-3-基）-4-芳基烟腈衍生物描述了在二氧化硅负载的高氯酸（HClO 4 -SiO 2）存在的条件下。重用催化剂的能力，高收率和易于纯化是该方法的重要特征。
• Facile One-Pot, Multicomponent Synthesis of Pyridines Under Microwave Irradiation
  作者：Jian-Feng Zhou、Yuan-Zhi Song、Jin-Shun Lv、Gui-Xia Gong、Shujiang Tu

  DOI：10.1080/00397910802531930

  日期：2009.3.25

  chromen-3-yl)-4-pyridine-3-carbo-nitriles were synthesized by the one-pot, multicomponent reaction of 3-acetyl-coumarin, aromatic aldehydes, malononitrile, and ammonium acetate in acetic acid under microwave irradiation. The reactions were completed in 10–13 min with 61–86% yields, were environmental benign, and had easy workup. Their structures were confirmed by 1H NMR, IR, and MS spectra and elemental

  摘要 通过3-乙酰香豆素的一锅多组分反应合成了一系列2-氨基-6-(2-oxo-2H-chromen-3-yl)-4-pyridine-3-carbo-nitriles,芳香醛、丙二腈和醋酸铵在微波辐射下的醋酸中。反应在 10-13 分钟内完成，产率为 61-86%，对环境无害，并且易于处理。它们的结构通过 1H NMR、IR、MS 光谱和元素分析得到证实。
• Iron(III) phosphate as a green and reusable catalyst for the synthesis of 4,6-disubstituted 2-aminopyridine-3-carbonitriles
  作者：Mahbobeh Zadpour、Farahnaz K. Behbahani

  DOI：10.1007/s00706-015-1456-1

  日期：2015.11

  Condensation reaction of aryl aldehydes, methyl ketones, malononitrile, and ammonium acetate in the presence of the green and recyclable catalyst FePO4 affords the corresponding 4,6-disubstituted 2-aminopyridine-3-carbonitriles. Some new derivatives of these compounds are synthesized. The catalyst can be also recycled and reused several times.[GRAPHICS].
• Magnetic cellulose/Ag as a novel eco-friendly nanobiocomposite to catalyze synthesis of chromene-linked nicotinonitriles
  作者：Ali Maleki、Hamed Movahed、Parisa Ravaghi

  DOI：10.1016/j.carbpol.2016.09.002

  日期：2017.1

  In this work, design, preparation and performance of magnetic cellulose/Ag nanobiocomposite as a recyclable and highly efficient heterogeneous nanocatalyst is described. Fourier transform infrared (FT-IR) spectroscopy, X-ray diffraction (XRD) pattern, vibrating sample magnetometer (VSM) curve, field-emission scanning electron microscopy (FE-SEM) image, energy dispersive X-ray (EDX) analysis and thermogravimetric analysis/differential thermal analysis (TGA/DTA) were used for the characterization. Then, its activity was investigated in the synthesis of 2-amino-6-(2-oxo-2H-chromen3-yl)-4-phenylnicotinonitrile derivatives. The main advantages of the reaction are high yields and short reaction times. The remarkable magnetic property of the nanobiocomposite catalyst provides easy separation from the reaction mixture by an external magnet without considerable loss of its catalytic activity. (C) 2016 Elsevier Ltd. All rights reserved.