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

• 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-(4-nitrophenyl)nicotinonitrile
• 英文别名: 2-Amino-4-(4-nitrophenyl)-6-(2-oxochromen-3-yl)pyridine-3-carbonitrile
• 化学式: C₂₁H₁₂N₄O₄
• 分子量: 384.351
• InChiKey: RYIUVIVUCSYHDZ-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

• 作为反应物：
  描述：

  2-amino-6-(2-oxo-2H-chromen-3-yl)-4-(4-nitrophenyl)nicotinonitrile 在 sodium acetate 、 potassium carbonate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Adamantane-pyrido[2,3-d]pyrimidine Derivatives; Synthesis, Characterization and Investigation of Antimicrobial Study

  摘要：

  制备了基于金刚烷-吡啶并[2,3-d]嘧啶衍生物的靶分子。以 N-(羟基金刚烷-1-基)-5-(2,4-取代苯基)-2-甲基-4-氧代-7-(2-氧代-2H-色烯-3-基)吡啶并[2、3-(2-氯乙酰基)-5-(2,4-取代苯基)-2-甲基-7-(2-氧代-2H-色烯-3-基)吡啶并[2,3-d]嘧啶-4(3H)-酮 (5a-j) 与 3-氨基金刚烷-1-醇反应合成了金刚烷酰胺 (6a-j)。这些金刚烷-吡啶并[2,3-d]嘧啶衍生物对临床分离的菌株进行了体外生物特性研究，并通过傅立叶变换红外光谱、1H-NMR、13C NMR 和 LCMS 对其结构进行了确认。新合成的衍生物具有良好的抗菌活性。

  DOI：

  10.13005/ojc/390219
• 作为产物：
  描述：

  3-乙酰基香豆素 在 乙酸铵 、 三乙胺 作用下， 以 乙醇 为溶剂， 生成 2-amino-6-(2-oxo-2H-chromen-3-yl)-4-(4-nitrophenyl)nicotinonitrile
  参考文献：
  名称：

  一些新香豆素衍生物的合成及抗抑郁活性

  摘要：

  香豆素-3-肉桂酰基衍生物2a-d是通过3-乙酰基香豆素1与不同的芳族醛的克莱森-施密特缩合制备的。2b，e与胍和硫脲的环加成反应分别得到相应的氨基嘧啶3a，b和硫代嘧啶衍生物4a，b。将化合物4a，b与氯乙酸或3-溴丙酸缩合，分别得到香豆素3-噻唑并嘧啶5a，b和噻嗪并嘧啶6a，b的衍生物。将化合物4a，b与氯乙酸和芳族醛缩合，得到芳基亚甲基衍生物7a，b，其可以通过化合物5a，b与芳族醛的缩合直接制备。在乙酸铵存在下，将化合物2a-e与丙二腈或乙酸氰基乙酯缩合，得到氰基吡啶8a，b和氰基吡啶酮9a-d衍生物，它们是通过3-乙酰香豆素1，丙二腈或氰基乙酸乙酯与乙酸醛存在下的芳族醛缩合而制得的。化合物2a，b，e与邻苯二胺在回流的乙醇中缩合导致形成10a-c作为中间体，然后通过热解裂解为苯并咪唑衍生物11以及化合物12a-c作为混合物，它们是通过熔融直接获得的在200-220℃下用α-不饱

  DOI：

  10.3797/scipharm.aut-05-15

文献信息

• A novel and reusable ionically tagged nanomagnetic catalyst: Application for the preparation of 2-amino-6-(2-oxo-2H-chromen-3-yl)-4-arylnicotinonitriles via vinylogous anomeric based oxidation
  作者：Fatemeh Karimi、Mohammad Ali Zolfigol、Meysam Yarie

  DOI：10.1016/j.mcat.2018.11.009

  日期：2019.2

  Herein, we report Fe3O4@O2PO2(CH2)2NH3+CF3CO2− as a novel and reusable ionically tagged nanomagnetic catalyst. It was characterized by several techniques including Fourier transform infrared (FT-IR) spectroscopy, thermo gravimetric analysis/differential thermal analysis (TGA/DTA), scanning electron microscopy (SEM), transmission electron microscopy (TEM), vibrating sample magnetometer (VSM) and energy

  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。
• 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.