2-(4-oxobenzo[d][1,2,3]triazin-3(4H)-yl)acetamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并-1,2,3-三嗪类化合物
• 英文名称: 2-(4-oxobenzo[d][1,2,3]triazin-3(4H)-yl)acetamide
• 英文别名: 3-carbamoylmethyl-1,2,3-benzotriazin-4(3H)-one；3-(carbamoylmethyl)-1,2,3-benzotriazin-4-one；2-(4-Oxo-1,2,3-benzotriazin-3-yl)acetamide
• 化学式: C₉H₈N₄O₂
• mdl: MFCD06380296
• 分子量: 204.188
• InChiKey: JUMYJFSJDBZRGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  88.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氨基苯甲酸乙酯 在 盐酸 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 反应 1.5h， 生成 2-(4-oxobenzo[d][1,2,3]triazin-3(4H)-yl)acetamide
  参考文献：
  名称：

  1-Aryl-3-(carbamoylmethyl)triazenes:  Synthesis, Spectroscopic Analysis and Cyclization to New 1,2,3-Benzotriazines

  摘要：

  Reaction of a series of arene diazonium salts with glycinamide affords the N-coupling products the 1-aryl-3-(carbamoylmethyl)triazenes, ArN=NNHCH2CONH2 3, which have been characterized by H-1 and C-13 NMR spectroscopy. The reaction works well with electron withdrawing groups in the ortho- or para-position of the aryl moiety, but when the coupling reaction was attempted with a p-bromo-substituted diazonium salt, the reaction afforded the pentazadiene 8 and not the expected triazene. Triazenes with a reactive ester or cyano-substituent in the ortho-position of the benzene ring were found to undergo spontaneous cyclization to the respective 1,2,3-benzotriazine heterocycles 4a and 5. The 3-(carbamoylmethyl)-4-imino-1,2,3-benzotriazine (5) was characterized by further NMR experiments, N-15 NMR, and homonuclear correlated NMR spectra.

  DOI：

  10.1021/jo951279i

文献信息

• A15N NMR investigation of a series of benzotriazinones and related antitumour heterocycles
  作者：Keith Vaughan、Derry E. V. Wilman、Richard T. Wheelhouse、Malcolm F. G. Stevens

  DOI：10.1002/mrc.994

  日期：2002.4

  A series of 3‐substituted 1,2,3‐benzotriazin‐4‐ones, 1 and 2, were synthesized by standard methods and the 15N NMR spectra were recorded. All spectra were obtained using the natural abundance of the nitrogen‐15 isotope. The chemical shifts appear in the normal range for N‐1, N‐2 and N‐3 of the triazine ring, and also correlate with the chemical shifts in the spectra of the imidazolotriazinone, 4, and

  通过标准方法合成了一系列 3-取代的 1,2,3-苯并三嗪-4-酮，1 和 2，并记录了 15N NMR 光谱。所有光谱均使用氮 15 同位素的天然丰度获得。三嗪环的 N-1、N-2 和 N-3 的化学位移出现在正常范围内，并且还与咪唑并三嗪酮 4 和咪唑并四嗪酮 5 光谱中的化学位移相关。 1a、2 和 4 的光谱，用完整的 NOE 记录，显示分配给 N-3 的单线态的反转，证明这些化合物以所示的互变异构形式存在。15N NMR 分析证实了 4-亚氨基苯并三嗪酮 (3) 的结构。光谱显示了带有 NH 的亚氨基氮原子的信号，它是 NOE 光谱中的倒置单线态，而来自 3 的 N-3 原子的信号在 NOE 光谱中没有反转。版权所有 © 2002 John Wiley & Sons, Ltd.
• Antiviral Drugs for Treatment or Prevention of Dengue Infection
  申请人：Byrd Chelsea M.

  公开号：US20100189685A1

  公开（公告）日：2010-07-29

  Compounds, methods and pharmaceutical compositions for treating viral infections, by administering certain compounds in therapeutically effective amounts are disclosed. Methods for preparing the compounds and methods of using the compounds and pharmaceutical compositions thereof are also disclosed. In particular, the treatment and prophylaxis of viral infections such as caused by flavivirus is disclosed, i.e., including but not limited to, Dengue virus, West Nile virus, yellow fever virus, Japanese encephalitis virus, and tick-borne encephalitis virus.
• 1-Aryl-3-(carbamoylmethyl)triazenes:  Synthesis, Spectroscopic Analysis and Cyclization to New 1,2,3-Benzotriazines
  作者：Jason V. Jollimore、Keith Vaughan、Donald L. Hooper

  DOI：10.1021/jo951279i

  日期：1996.1.1

  Reaction of a series of arene diazonium salts with glycinamide affords the N-coupling products the 1-aryl-3-(carbamoylmethyl)triazenes, ArN=NNHCH2CONH2 3, which have been characterized by H-1 and C-13 NMR spectroscopy. The reaction works well with electron withdrawing groups in the ortho- or para-position of the aryl moiety, but when the coupling reaction was attempted with a p-bromo-substituted diazonium salt, the reaction afforded the pentazadiene 8 and not the expected triazene. Triazenes with a reactive ester or cyano-substituent in the ortho-position of the benzene ring were found to undergo spontaneous cyclization to the respective 1,2,3-benzotriazine heterocycles 4a and 5. The 3-(carbamoylmethyl)-4-imino-1,2,3-benzotriazine (5) was characterized by further NMR experiments, N-15 NMR, and homonuclear correlated NMR spectra.