2,9-dimethyl-1,3-dioxo-1,3-dihydropyrrolo<3,4-b>quinoline | 77705-51-2

• 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: 2,9-dimethyl-1,3-dioxo-1,3-dihydropyrrolo<3,4-b>quinoline
• 英文别名: 2,9-dimethyl-1,3-dioxo-1,3-dihydropyrrolo[3,4-b]quinoline；2,9-dimethylpyrrolo[3,4-b]quinoline-1,3-dione
• CAS: 77705-51-2
• 化学式: C₁₃H₁₀N₂O₂
• 分子量: 226.235
• InChiKey: MNAVVVNHOIWFGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.77
• 重原子数：
  17.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  50.27
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  diethyl (E)-2-(2-acetylanilino)but-2-enedioate 、 甲胍 以10%的产率得到
  参考文献：
  名称：

  KURASAWA YOSHIHISA; TAKADA ATSUSHI, CHEM. AND PHARM. BULL., 1980, 28, NO 12, 3457-3465

  摘要：

  DOI：

文献信息

• A convenient synthesis of pyridazino(4,5-b)quinolines and pyrrolo(3,4-b)quinolines.
  作者：YOSHIHISA KURASAWA、ATSUSHI TAKADA

  DOI：10.1248/cpb.28.3457

  日期：——

  The reaction of N-(1, 2-bisethoxycarbonylvinyl)-o-aminoacetophenone (IVc) with an excess of hydrazines or guanidines gave 4-hydroxy-1-oxo-1, 2-dihydropyridazino [4, 5-b]-quinolines (Ia, b) or 1, 3-dioxo-1, 3-dihydropyrrolo [3, 4-b] quinolines (IIIc, d), respectively. It was found that 2, 3-bishydrazinocarbonyl-4-methylquinolines (VIa, b) were converted to 4-hydroxy-1-oxo-1, 2-dihydropyridazino [4, 5-b] quinolines (Ia, b) and 1, 3-dioxo-1, 3-dihydropyrrolo [3, 4-b] quinolines (IIIa, b) under different reaction conditions.

  N-(1, 2-二乙氧基羰基乙烯基)-邻氨基苯乙酮 (IVc) 与过量的肼或胍反应，得到 4-羟基-1-氧代-1, 2-二氢哒嗪基[4, 5-b]-喹啉（分别为Ia、b)或1, 3-二氧代-1, 3-二氢吡咯并[3, 4-b]喹啉(IIIc, d)。发现2, 3-双肼基羰基-4-甲基喹啉(VIa, b)转化为4-羟基-1-氧代-1, 2-二氢哒嗪基[4, 5-b]喹啉(Ia, b)和1,不同反应条件下的3-二氧代-1, 3-二氢吡咯并[3, 4-b]喹啉(IIIa, b)。
• Copper(II)-Catalyzed Synthesis of Pyrrolo[3,4-<i>b</i>]quinolinediones from <i>o</i>-Amino Carbonyl Compounds and Maleimides
  作者：Dhananjay S. Nipate、Krishnan Rangan、Anil Kumar

  DOI：10.1021/acs.orglett.3c00240

  日期：2023.3.3

  A copper(II)-catalyzed cascade synthesis of 1H-pyrrolo[3,4-b]quinoline-1,3(2H)-diones has been achieved from readily available o-amino carbonyl compounds and maleimides. This one-pot cascade strategy involves a copper-catalyzed aza-Michael addition followed by condensation and oxidation to deliver the target molecules. The protocol features a broad substrate scope and excellent functional group tolerance

  铜 (II) 催化的 1 H-吡咯并 [3,4- b ] 喹啉-1,3(2 H )-二酮的级联合成已经从容易获得的邻氨基羰基化合物和马来酰亚胺中实现。这种单锅级联策略涉及铜催化的氮杂-迈克尔加成，然后进行缩合和氧化以传递目标分子。该协议具有广泛的底物范围和出色的官能团耐受性，并提供中等至良好 (44–88%) 产量的产品。
• PhIO Mediated One‐Pot Synthesis of Pyrroloquinolinediones from <i>ortho</i>‐Carbonyl Anilines and Maleimides
  作者：Mohammed Issa Alahmdi、Sayeed Mukhtar、Humaira Parveen、Meshari A. Alsharif、Mohd Waheed

  DOI：10.1002/ejoc.202400074

  日期：2024.3

  A simple, green and metal-free hypervalent iodine mediated approach for the synthesis of pyrroloquinolinediones from ortho-carbonyl anilines and maleimides in one-pot manner at room temperature has been developed. H2O as the only by-product generated during the reaction, displays a high atom economy.

  开发了一种简单、绿色、无金属的高价碘介导的方法，用于在室温下以邻羰基苯胺和马来酰亚胺为原料以一锅法合成吡咯并喹啉二酮。H 2 O作为反应过程中产生的唯一副产物，表现出较高的原子经济性。