4,5-dihydro-5-methyl-4-oxotetrazolo<1,5-a>quinoxaline | 29067-89-8

• 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: 4,5-dihydro-5-methyl-4-oxotetrazolo<1,5-a>quinoxaline
• 英文别名: 5-methyltetrazolo[1,5-a]quinoxalin-4(5H)-one；5-methyl-5H-tetrazolo[1,5-a]quinoxalin-4-one；5-Methyltetrazolo[1,5-a]quinoxalin-4-one
• CAS: 29067-89-8
• 化学式: C₉H₇N₅O
• 分子量: 201.187
• InChiKey: HBCLKTATADWKFU-UHFFFAOYSA-N

物化性质

• 熔点：
  240-241 °C
• 沸点：
  470.0±28.0 °C(Predicted)
• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  63.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,5-dihydro-5-methyl-4-oxotetrazolo<1,5-a>quinoxaline 在 copper(II) acetate monohydrate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以49 %的产率得到3-氨基-1-甲基-2(1H)-喹喔啉酮
  参考文献：
  名称：

  Convergent Paired Electrolysis for [3+2] Cycloaddition of Azidotrimethylsilane with N‐Heterocycles

  摘要：

  A widely used method to obtain tetrazoles is through the azide and nitrile [3+2] cycloaddition. However, this process often involves using non‐recyclable transition metals or Lewis acid catalysts and stoichiometric amounts of oxidants and additives, which reduces atom efficiency. We have discovered a convergent paired electrochemical reaction to perform this cycloaddition reaction, without the need for metal catalysts or oxidants. This tetrazolation strategy uses azidotrimethylsilane (TMSN3) and N‐heterocycles in an undivided cell at a constant current. We use a mixture of CH3CN and equivalent amounts of H2O as co‐solvent at room temperature. It is crucial to produce a stoichiometric amount of active hydroxyl ions through the cathodic reduction of water. Cyclic voltammetry (CV) studies and control experiments confirm that the cycloaddition reaction is specific to the electrode electron transfer process, eliminating the need for a mediator to shuttle electrons. This metal‐ and oxidant‐free strategy is highly compatible with different functional groups and produces products with moderate to good yields. We have successfully tetrazolated bioactive compounds at a late stage, scaled up batches efficiently, and synthesized free amino‐containing N‐heterocycles via denitrogenation of tetrazoles.

  DOI：

  10.1002/cssc.202400381
• 作为产物：
  描述：

  3,3-diazido-1-methylindolin-2-one 以 邻二甲苯 为溶剂， 反应 2.0h， 以96%的产率得到4,5-dihydro-5-methyl-4-oxotetrazolo<1,5-a>quinoxaline
  参考文献：
  名称：

  四唑的合成路线：偕二叠氮化物的热解

  摘要：

  描述了一种新的四唑核心合成路线，该路线基于在一系列具有偕二叠氮基单元的化合物中发现的一般断裂模式。通过简单的两步程序，从广泛可用的底物（即羟吲哚、二芳基乙酮、吡唑啉酮和菲酚）开始，可以轻松合成含有四唑的结构多样的目标化合物，例如四唑并喹喔啉酮、苯甲酰芳基四唑、四唑并三嗪酮和四唑并氮杂酮。 ）。在温和条件下与碘和叠氮化钠发生初始氧化重氮化反应，然后在微波辐射下发生热裂解，产生四唑产物。值得注意的是，提出了一种实验解决方案，其中没有分离出潜在危险的二叠氮中间体，并且不需要浓缩含有二叠氮的粗反应混合物即可以良好的产率获得四唑。

  DOI：

  10.1002/chem.201902131

文献信息

• [3+2] Cyclization of Azidotrimethylsilane with Quinoxalin-2(1<i>H</i> )-Ones to Synthesize Tetrazolo[1,5-<i>a</i> ]quinoxalin-4(5<i>H</i> )-Ones
  作者：Qiming Yang、Yuecheng Zhang、Qian Sun、Kun Shang、Hong-Yu Zhang、Jiquan Zhao

  DOI：10.1002/adsc.201801076

  日期：2018.12.3

  protocol for the synthesis of thetetrazolo[1,5‐a]quinoxalin‐4(5H)‐ones via copper‐catalyzed [3+2] cyclization of azidotrimethylsilane with quinoxalin‐2(1H)‐ones under mild conditions has been disclosed. This practical protocol is compatible with a variety of functional groups and provides an access to functionalized tetrazolo[1,5‐a]quinoxalin‐4(5H)‐ones from readily available and safe starting materials

  一种方便有效的方案，在温和的条件下，用喹喔啉-2（1 H）-1通过铜催化的叠氮三甲基硅烷的[ 3 + 2]环化反应合成四唑并[1,5 - a ]喹喔啉-4（5 H）-1。条件已经公开。该实用协议与各种官能团兼容，并提供了从容易获得的安全起始原料中获得功能化四唑[1,5 - a ]喹喔啉-4（5 H）-的方法。
• Direct C( <i>sp</i> ² )−H Amination to Synthesize Primary 3‐aminoquinoxalin‐2(1 <i>H</i> )‐ones under Simple and Mild Conditions
  作者：Qiming Yang、Zibing Yang、Yushi Tan、Jiquan Zhao、Qian Sun、Hong‐Yu Zhang、Yuecheng Zhang

  DOI：10.1002/adsc.201801661

  日期：2019.4

  A convenient C−H amination of quinoxalin‐2‐ones has been developed. This transformation provides concise access to 3‐aminoquinoxalin‐2(1H)‐ones with a broad tolerance of functional groups, utilizing TMSN3 as an amino source under simple and mild conditions. The target 3‐aminoquinoxalin‐2(1H)‐ones are important intermediates for the synthesis of biologically active 3‐N‐substituted quinoxalin‐2‐one derivatives

  已开发出方便的喹喔啉-2-酮的CH胺化反应。通过在简单温和的条件下利用TMSN 3作为氨基源，这种转化提供了对具有广泛官能团耐受性的3-氨基喹喔啉-2（1 H）-的简明访问。目标3-氨基喹喔啉-2-（1 H）-1是合成具有生物活性的3 - N取代的喹喔啉-2-酮衍生物的重要中间体。
• Makino, Kenzi; Sakata, Gozyo; Morimoto, Katsushi, Heterocycles, 1985, vol. 23, # 8, p. 2025 - 2034
  作者：Makino, Kenzi、Sakata, Gozyo、Morimoto, Katsushi

  DOI：——

  日期：——
• Klicnar, Jiri; Toman, Jaromir, Collection of Czechoslovak Chemical Communications, 1981, vol. 46, # 9, p. 2110 - 2115
  作者：Klicnar, Jiri、Toman, Jaromir

  DOI：——

  日期：——
• MAKINO, KENZI;SAKATA, GOZYO;MORIMOTO, KATSUSHI;OCHIAI, TOSHINORI, HETEROCYCLES, 1985, 23, N 8, 2025-2034
  作者：MAKINO, KENZI、SAKATA, GOZYO、MORIMOTO, KATSUSHI、OCHIAI, TOSHINORI

  DOI：——

  日期：——