6,7-dichloro-2-(4-methoxyphenyl)quinoxaline | 1220284-45-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 6,7-dichloro-2-(4-methoxyphenyl)quinoxaline
• 英文别名: 6,7-Dichloro-2-(4-methoxyphenyl)quinoxaline
• CAS: 1220284-45-6
• 化学式: C₁₅H₁₀Cl₂N₂O
• 分子量: 305.163
• InChiKey: GKVVURMJNDUZKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  35
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4,5-二氯邻苯二胺 、 4-甲氧基苯乙醛 在 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以67%的产率得到6,7-dichloro-2-(4-methoxyphenyl)quinoxaline
  参考文献：
  名称：

  Transition-Metal-Free Synthesis of Quinoxalines from o-Phenylenediamines and Arylacetaldehydes under Basic Conditions

  摘要：

  A novel method for the synthesis of quinoxalines via transition-metal-free cyclization of o-phenylenediamine and arylacetaldehyde in a one-pot procedure has been developed. In this process, an inorganic base (K2CO3) is the only reagent required, and it proceeds smoothly in the absence of adding transition metal catalysts. The reaction appears to be very general and suitable for the construction of a variety of quinoxalines.

  DOI：

  10.1055/s-0031-1290450

文献信息

• Visible light promoted tandem dehydrogenation-deaminative cyclocondensation under aerobic conditions for the synthesis of 2-aryl benzimidazoles/quinoxalines from <i>ortho</i>-phenylenediamines and arylmethyl/ethyl amines
  作者：Firdoos Ahmad Sofi、Rohit Sharma、Ravi Rawat、Asit K. Chakraborti、Prasad V. Bharatam

  DOI：10.1039/d0nj03002c

  日期：——

  Visible light promoted domino synthesis of 2-aryl benzimidazoles is reported through the reaction of ortho-phenylenediamines and arylmethyl amines under aerobic conditions. The methodology has wide substrate scope and tolerates a wide range of functional groups affording the products in high yields. The use of arylethyl amines instead of arylmethyl amines gives 2-aryl quinoxalines.

  据报道，通过有氧条件下邻苯二胺与芳基甲基胺的反应，可见光促进了2-芳基苯并咪唑的多米诺骨牌合成。该方法具有广泛的底物范围，并且可以耐受多种官能团，从而以高收率提供了产品。使用芳基乙基胺代替芳基甲基胺得到2-芳基喹喔啉。
• Synthesis of quinoxalines catalysed by cetyltrimethyl ammonium bromide (CTAB) in aqueous media
  作者：Tieqiang Huang、Qaing Zhang、Jiuxi Chen、Wenxia Gao、Jinchang Ding、Huayue Wu

  DOI：10.3184/030823409x12591655855261

  日期：2009.12

  A facile and simple method has been developed for the condensation of 1,2-diaminobenzenes with α-bromoketones to form quinoxalines with good yields using cetyltrimethyl ammonium bromide (CTAB) in aqueous media. The efficiency of this reaction was demonstrated by the compatibility with nitro, methyl, methoxy, fluoro chloro bromo and furanyl groups. The important features of the methodology are broad substrate scope, simple workup, and no requirement for metal catalysts.

  本研究采用十六烷基三甲基溴化铵（CTAB），在水介质中开发出了一种简便易行的方法，用于 1,2-二氨基苯与α-溴酮缩合生成喹喔啉类化合物，并取得了良好的收率。该反应与硝基、甲基、甲氧基、氟氯溴基和呋喃基的相容性证明了其高效性。该方法的重要特点是底物范围广、操作简单、无需金属催化剂。
• Transition-Metal-Free Synthesis of Quinoxalines from o-Phenylenediamines and Arylacetaldehydes under Basic Conditions
  作者：Baohua Chen、Jinli Song、Xiaolong Li、Yongxin Chen、Mingming Zhao、Yani Dou

  DOI：10.1055/s-0031-1290450

  日期：——

  A novel method for the synthesis of quinoxalines via transition-metal-free cyclization of o-phenylenediamine and arylacetaldehyde in a one-pot procedure has been developed. In this process, an inorganic base (K2CO3) is the only reagent required, and it proceeds smoothly in the absence of adding transition metal catalysts. The reaction appears to be very general and suitable for the construction of a variety of quinoxalines.