6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thidiazine | 22184-39-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thidiazine
• 英文别名: 6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine；7H-6-Phenyl-s-triazolo<3,4-b><1,3,4>thiadiazin；6-Phenyl-7H-1,2,4-triazolo<3.4-b>-1,3,4-thiadiazin；6-Phenyl-7h-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine
• CAS: 22184-39-0
• 化学式: C₁₀H₈N₄S
• mdl: MFCD00128577
• 分子量: 216.266
• InChiKey: FGJKILJJRFLVCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  68.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thidiazine 、 乙酸酐 反应 1.0h， 以71%的产率得到1-acetyl-7-acetylsulfanyl-6-phenyl-1H-pyrazolo[5,1-c][1,2,4]triazole
  参考文献：
  名称：

  Pyrolytic desulfurization ring contraction of condensed thiadiazines as a general route towards pyrazoloazines and pyrazoloazoles with a bridgehead (ring junction) nitrogen atom

  摘要：

  Pyrolytic conversion of [1,2,4]triazino[3,4-b][1,3,4]thiadiazin-4-ones, [1,3,4]thiadiazino[2,3-b]quinazolin-10-ones and [1,2,4]triazolo[3,4-b][1,3,4]thiadiazines into their corresponding pyrazolo[5,1-c][1,2,4]triazin-4-ones, Pyrazolo[4,3-b]quinazolin-9-ones and pyrazolo[5,1-b][1,2,4]triazoles via desulfurization ring contraction is described. The starting condensed 1,3,4-thiadiazines were prepared from the corresponding readily available 4-amino-3-thioxo-1,2,4-triazin-5(4H)-ones, 3-amino-2,3-dihydro-2-thioxo-quinazolin-4(1H)-one and 4-amino-3(2H)-thioxo-1,2,4-triazoles upon reaction with the appropriate alpha-haloketones in two steps, or directly in one step in ethylpyridinium tetrafluoroborate (ionic liquid, IL). (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.08.067
• 作为产物：
  描述：

  2-溴苯乙酮 在 三氟乙酸 作用下， 以 二甲基亚砜 为溶剂， 反应 13.0h， 生成 6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thidiazine
  参考文献：
  名称：

  有效合成7 H -1,2,4-三唑[3,4- b] [1,3,4]噻二嗪

  摘要：

  在芳基（杂芳基）α-溴代酮缩合反应的基础上，开发了一种高效的7 H -1,2,4-三唑并[3,4- b ] [1,3,4]噻二嗪的制备方法然后，在温和条件下，在三氟乙酸存在下，用原酸酯处理所得的2-肼基-6 H -1,3,4-噻二嗪氢溴酸盐。

  DOI：

  10.1007/s10593-018-2325-8

文献信息

• Solid Acid Induced Cyclocondensation: A Facile, One-Pot Synthesis of 7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines
  作者：M. M. Heravi、M. Bakherad、M. Rahimzadeh、M. Bakavoli

  DOI：10.1080/10426500214303

  日期：2002.10

  7H-[1,2,4]Triazolo[3,4-b][1,3,4]thiadiazines are synthesized in good yields by the catalytic action of sulfuric acid adsorbed on sillica gel. Starting from 4-amino-5-substituted-1,2,4-triazole-3-thiones and employing cyclocondensation reaction with f -chloroacetonitrile and f -haloketones, the desired triazolothiadiazines have been synthesized satisfactorilly.

  7H-[1,2,4]三唑并[3,4-b][1,3,4]噻二嗪通过吸附在硅胶上的硫酸的催化作用以良好的产率合成。以4-氨基-5-取代-1,2,4-三唑-3-硫酮为原料，与f-氯乙腈和f-卤代酮进行环缩缩合反应，成功合成了所需的三唑噻二嗪。
• α,α-Dibromoacetophenones mediated synthesis of some new 7H-7-alkoxy-3-alkyl/phenyl-6-aryl-s-triazolo[3,4-b][1,3,4]thiadiazines and their antimicrobial evaluation
  作者：Rashmi Pundeer、Vijay Kiran、Richa Prakash、Sushma、Subhash C. Bhatia、Chetan Sharma、Kamal R. Aneja

  DOI：10.1007/s00044-011-9945-1

  日期：2012.12

  A series of new 7H-7-alkoxy-3-alkyl/phenyl-6-aryl-s-triazolo[3,4-b][1,3,4]thiadiazines (3, 4) were synthesized by the reaction of various alpha,alpha-dibromoacetophenones 1 with 3-alkyl/phenyl-4-amino-5-mercapto-s-triazoles (2) in different alcoholic solvents in good yields. All the newly synthesized compounds (3, 4) were screened for their in vitro antibacterial and antifungal activity. Biological activities of these compounds were compared with those of the commercially available antibiotic, ciprofloxacin and antifungal agent, amphotericin-B. The title compounds showed good activity against the Gram-positive bacteria, Staphylococcus aureus and Bacillus subtilis and the yeasts, Saccharomyces cerevisiae and Candida albicans.
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