6-amino-[1,3]dioxolo[4,5-g]quinoline-7-carbonitrile | 209533-66-4

• 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: 6-amino-[1,3]dioxolo[4,5-g]quinoline-7-carbonitrile
• 英文别名: 1,3-Dioxolo[4,5-g]quinoline-7-carbonitrile, 6-amino-
• CAS: 209533-66-4
• 化学式: C₁₁H₇N₃O₂
• 分子量: 213.195
• InChiKey: HLYDXNRVWCEUNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  81.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,.4-Methylenedioxy-6-nitrobenzylidene malononitrile 在 四氯化钛 、 锌 作用下， 以 四氢呋喃 为溶剂， 以78%的产率得到6-amino-[1,3]dioxolo[4,5-g]quinoline-7-carbonitrile
  参考文献：
  名称：

  Facile and Efficient Synthesis of 2-Aminoquinoline-3-carboxylic Acid Derivatives via Reductive Cyclization of Nitro and Cyano Groups Induced by Low-valent Titanium

  摘要：

  通过四氯化钛/锌促进的硝基氰基烯烃的分子内还原环化反应，成功实现了一系列2-氨基喹啉-3-羧酸衍生物的简便且高效的合成，产率良好。

  DOI：

  10.1039/a800588e

文献信息

• Low-Valent Titanium Induced Reductive Coupling of Nitriles with Nitro Compounds
  作者：Longhu Zhou、Yongmin Zhang

  DOI：10.1080/00397919808004430

  日期：1998.9

  Abstract The intermolecular and intramolecular reductive coupling of a cyano group with a nitro group induced by a low-valent titanium reagent prepared from TiCl4/Sm was studied. Amidines and 2-aminoquinolines derivatives are preparied in good yields under mild conditions respectively.

  摘要 研究了由TiCl4/Sm 制备的低价钛试剂诱导氰基与硝基的分子间和分子内还原偶联。脒和 2-氨基喹啉衍生物分别在温和条件下以良好的收率制备。
• A novel reductive cyclization of arylmethylidenemalononitrile promoted by samarium diiodide
  作者：Longhu Zhou、Yongmin Zhang

  DOI：10.1039/a802510j

  日期：——

  The intermolecular and intramolecular reductive coupling reactions of arylmethylidenemalononitriles induced by SmI2 have been studied. The configuration of the cyclodimerization products, 4,5-trans-isomers of 2-amino-1,3,3-tricyano-4,5-diarylcyclopentenes, has been confirmed by X-ray analysis and a possible reaction mechanism is proposed.

  已经研究了由SmI2诱导的芳基甲叉马龙腈的分子间和分子内还原偶联反应。通过X射线分析确认了环二聚化产物的构型，即2-氨基-1,3,3-三氰基-4,5-二芳基环戊烯的4,5-反式异构体，并提出了一种可能的反应机制。
• <scp> NH ₄ Cl </scp> /Zn powder: An efficient, chemoselective reducing catalyst for the microwave‐assisted synthesis of 2,3‐disubstituted quinolines via tandem Knoevenagel condensation
  作者：Syed Tasqeeruddin、Yahya I. Asiri、Syeda Shaheen

  DOI：10.1002/jhet.4203

  日期：2021.2

  An efficient, a hitherto unreported, sustainable, and environmentally friendly microwave‐assisted synthesis of 2,3‐disubstituted quinolines by reductive cyclization of 2‐nitrobenzaldehydes and various active methylene compounds via tandem Knoevenagel condensation promoted by an efficient eco‐friendly, chemoselective reducing catalyst ammonium chloride (NH4Cl) and zinc powder was developed. This present

  通过2-硝基苯甲醛和各种活性亚甲基化合物通过串联的Knoevenagel缩合反应进行的高效环合缩合反应，通过高效的生态友好型，化学选择性还原催化剂促进的高效，迄今未报道的，可持续的，环境友好的微波辅助合成2,3-二取代的喹啉开发了氯化铵（NH 4 Cl）和锌粉。本方法学是一种温和，绿色，高效且对环境有益的方法，因为它消除了苛刻的反应条件，非挥发性溶剂，相对昂贵的试剂，高催化剂负载量，并且还提供了许多其他好处，例如快速合成，简单反应设置，并达到产品的优异产量。
• A NOVEL REDUCTIVE CYCLIZATION OF ARYLMETHYLIDENEMALONONITRILE PROMOTED BY LOW-VALENT TITANIUM
  作者：Daqing Shi、Hong Zhao、Xiangshan Wang、Changsheng Yao、Longhu Zhou

  DOI：10.1081/scc-120014037

  日期：2002.1

  The intermolecular and intramolecular reductive coupling reactions of arylmethylidenemalononitriles induced by low-valent titanium have been studied. A possible reaction mechanism is proposed.
• Low-Valent Titanium Induced Novel Reductive Cyclization of α,β-Unsaturated Nitrile Compounds
  作者：Long-hu Zhou、Shu-jiang Tu、Da-qin Shi、Gui-yuan Dai、Wei-xing Chen

  DOI：10.1055/s-1998-2082

  日期：1998.6