3-methyl-6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]-thiadiazine | 54025-94-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-methyl-6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]-thiadiazine
• 英文别名: 3-methyl-6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine；3-methyl-6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin；3-methyl-6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thidiazine；3-methyl-6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine；3-Methyl-6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin
• CAS: 54025-94-4
• 化学式: C₁₁H₁₀N₄S
• mdl: MFCD00128574
• 分子量: 230.293
• InChiKey: VMPIHHBGVRZILQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.181
• 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：

  3-methyl-6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]-thiadiazine 、 乙酸酐 反应 1.0h， 以75%的产率得到1-acetyl-7-acetylsulfanyl-3-methyl-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：

  4-氨基-5-甲基-4H-3-巯基-1,2,4-三唑 以65%的产率得到
  参考文献：
  名称：

  DHAKA K. S.; MOHAN J.; CHADHA V. K.; PUJARI H. K., INDIAN J. CHEM. , 1974, 12, NO 3, 287-289

  摘要：

  DOI：

文献信息

• Effective synthesis of 7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazines
  作者：Alexander S. Kulikov、Margarita A. Epishina、Leonid L. Fershtat、Nina N. Makhova

  DOI：10.1007/s10593-018-2325-8

  日期：2018.6

  A highly effective method for the preparation of 7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazines was developed on the basis of condensation reaction between aryl(hetaryl) α-bromo ketones and commercially available thiocarbohydrazide, followed by treatment of the obtained 2-hydrazinyl-6H-1,3,4-thiadiazine hydrobromides with ortho esters in the presence of trifluoroacetic acid under mild conditions.

  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。
• Heteropolyacides as green and reusable catalysts for the synthesis of [3,4-<i>b</i>][1,3,4] thiadiazines
  作者：F. Hakimi、A. Hassanabadi、M. Tabatabaee、M. M. Heravi

  DOI：10.4314/bcse.v28i1.8

  日期：——

  Synthesis of [3,4-b][1,3,4]thiadiazines from the condensation of 4-amino-6-methyl-3-thioxo-1,2,4-triazine-5(2H)-one (AMTTO) or 4-amino-1,4-dihydro-5-methyle-1,2,4-triazole-5-thione (AMTT) with phenacyl bromide in the presence of a catalytic amount of various heteropolyacids (HPAs) under refluxing conditions is reported.

  报告了在回流条件下，4-氨基-6-甲基-3-硫酮-1,2,4-三嗪-5(2H)-酮 (AMTTO) 或 4-氨基-1,4-二氢-5-甲基-1,2,4-三唑-5-硫酮 (AMTT) 与苯乙酰溴在一定量的各种杂多酸 (HPA) 催化下缩合合成 [3,4-b][1,3,4]噻二嗪的过程。
• 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。
• Song, Ming-Xia; Zhang, Chun-Bo; Deng, Xian-Qing, Letters in drug design and discovery, 2011, vol. 8, # 9, p. 769 - 773
  作者：Song, Ming-Xia、Zhang, Chun-Bo、Deng, Xian-Qing、Sun, Zhi-Gang、Quan, Zhe-Shan

  DOI：——

  日期：——
• Dhaka,K.S. et al., Indian Journal of Chemistry, 1974, vol. 12, p. 287 - 289
  作者：Dhaka,K.S. et al.

  DOI：——

  日期：——