5,7-dimethyltetrahydro-1H-imidazo[4,5-e]-1,2,4-triazine-3,6(2H,4H)-dithione | 1247148-66-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 5,7-dimethyltetrahydro-1H-imidazo[4,5-e]-1,2,4-triazine-3,6(2H,4H)-dithione
• 英文别名: 5,7-dimethyl-2,4,4a,7a-tetrahydro-1H-imidazo[4,5-e][1,2,4]triazine-3,6-dithione
• CAS: 1247148-66-8
• 化学式: C₆H₁₁N₅S₂
• 分子量: 217.319
• InChiKey: APJSTSNSOFDPEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,7-dimethyltetrahydro-1H-imidazo[4,5-e]-1,2,4-triazine-3,6(2H,4H)-dithione 在 sodium acetate 、 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 反应 2.08h， 生成
  参考文献：
  名称：

  Synthesis of imidazo[4,5-e][1,3]thiazolo-[3,2-b][1,2,4]triazines

  摘要：

  Perhydroimidazo[4,5-e][1,2,4]triazine-3-thiones are alkylated with bromoacetic acid to give previously unreported imidazo[4,5-e][1,3]thiazolo[3,2-b][1,2,4]triazines whose structure has been confirmed by X-ray structural analysis.

  DOI：

  10.1007/s10593-012-1147-3
• 作为产物：
  描述：

  [[5-(2-Carbamothioylhydrazinyl)-1,3-dimethyl-2-sulfanylideneimidazolidin-4-yl]amino]thiourea 在 盐酸 、 苯甲醛 作用下， 以 甲醇 为溶剂， 生成 5,7-dimethyltetrahydro-1H-imidazo[4,5-e]-1,2,4-triazine-3,6(2H,4H)-dithione
  参考文献：
  名称：

  巯基尿嘧啶前体的意外形成

  摘要：

  出乎意料的是，亚硝酸钠在冰醋酸AcOH中将5,7-二烷基-3-硫代过氧氢杂咪唑[4,5- e ] -1,2,4-三嗪-6-酮（硫酮）亚硝化导致3,3'-bis（自发分解的5,7-二烷基-1-亚硝基-6-氧代（硫代）-1,4,4a，5,7,7a-六氢咪唑[4,5-e] -1,1,2,4-三嗪基）二硫化物在水存在下，在DMSO-d 6中转化为1,3-二烷基-5-硫代六氢咪唑并[4,5- d ]咪唑-2（1 H）-ones（thiones）。

  DOI：

  10.1002/jhet.2305

文献信息

• α-Thioureidoalkylation of urea heteroanalogs
  作者：G._A. Gazieva、Yu. V. Nelyubina、A. N. Kravchenko、A. S. Sigachev、I. V. Glukhov、M. I. Struchkova、K. A. Lyssenko、N. N. Makhova

  DOI：10.1007/s11172-009-0266-1

  日期：2009.9

  α-Thioureidoalkylation of urea heteroanalogs such as thiosemicarbazide, amino-guanidine, sulfamide, and sulfonamides with 4,5-dihydroxyimidazolidine-2-thiones has been studied. Previously unknown 4,5-bis[thiosemicarbazido(guanidinoamino)]imidazolidine-2-thiones, 5,7-dialkylperhydroimidazo[4,5- e][1,2,4]triazine-3,6-dithiones, 4,6-diethyl-5(3H)-thioxotetrahydro-1 H-imidazo[4,5- c][1,2,5]thiadiazole 2,2-dioxide, and 1,3-dialkyl-4-[guanidinoimino(arylsulfonylimino)]imidazolidine-2-thiones have been synthesized.

  研究人员对 4,5-二羟基咪唑烷-2-硫酮与脲杂环类化合物（如硫代氨基脲、氨基胍、磺酰胺和磺酰胺）的α-硫脲基烷基化进行了研究。以前未知的 4,5-双[硫代氨基羰基（胍基氨基）]咪唑烷-2-硫酮、5,7-二烷基过氢咪唑并[4,5-e][1,2,4]三嗪-3,6-二硫酮、4、6-二乙基-5(3H)-硫代四氢-1 H-咪唑并[4,5-c][1,2,5]噻二唑 2,2-二氧化物，以及 1,3-二烷基-4-[胍基亚胺基（芳基磺酰亚胺）]咪唑烷-2-硫酮的合成。
• Protolytic and potential antithyroid properties of thioglycolurils and fused azolo-1,2,4-triazines
  作者：V. A. Ivolgina、L. D. Popov、G. A. Gazieva、A. N. Kravchenko

  DOI：10.1007/s11172-020-3024-z

  日期：2020.11

  The protolytic properties and reactions with molecular iodine and blood serum proteins of 5,7-dimethyltetrahydro-1H-imidazo[4,5-e]-1,2,4-triazine-3,6(2H,4H)-dithione and (R)-1,3-dialkyl-4-[(2-hydroxybenzylidene)amino]-5-thioxohexahydroimidazo[4,5-d]imidazol-2(1H)-ones were studied. These compounds exhibit different chemical reactivities towards molecular iodine. The binding constants between these

  5,7-二甲基四氢-1H-咪唑并[4,5-e]-1,2,4-三嗪-3,6(2H,4H)-二硫酮和(研究了 R)-1,3-二烷基-4-[(2-羟基苯亚甲基) 氨基]-5-thioxohexahydroimidazo[4,5-d]imidazol-2(1H)-ones。这些化合物对分子碘表现出不同的化学反应性。这些化合物与血清白蛋白之间的结合常数证明了这些化合物具有相当大的蛋白质亲和力。硫酮的特性使它们有希望作为抗甲状腺药物。
• Synthesis of imidazo[4,5-<i>e</i>][1,3]thiazino[2,3-<i>c</i>][1,2,4]triazines via a base-induced rearrangement of functionalized imidazo[4,5-<i>e</i>]thiazolo[2,3-<i>c</i>][1,2,4]triazines
  作者：Dmitry B Vinogradov、Alexei N Izmest’ev、Angelina N Kravchenko、Yuri A Strelenko、Galina A Gazieva

  DOI：10.3762/bjoc.19.80

  日期：——

  Abstract A series of imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazines was synthesized via a cascade sequence of hydrolysis and skeletal rearrangement of imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazin-7(8H)-ylidene)acetic acid esters in methanol upon treatment with excess KOH. Imidazo[4,5-e]thiazolo[3,2-b][1,2,4]triazin-6(7H)-ylidene)acetic acid esters are also suitable substrates for the reaction. In

  摘要 通过咪唑并[ 4,5- ]水解和骨架重排的级联序列合成了一系列咪唑并[4,5-e] [1,3]噻嗪[2,3- c ][1,2,4]三嗪e ]噻唑并[2,3- c ][1,2,4]三嗪-7(8H ) -亚基)乙酸酯在甲醇中用过量的KOH处理。咪唑并[4,5- e ]噻唑并[3,2- b ][1,2,4]三嗪-6(7H ) -亚基)乙酸酯也是该反应的合适底物。在这种情况下，水解和噻唑环扩张伴随着噻唑并三嗪连接类型从噻唑并[3,2- b ][1,2,4]三嗪转变为噻嗪并[2,3- c ][1,2,4 ]三嗪。 贝尔斯坦 J. 组织。化学。 2023, 19, 1047–1054。doi:10.3762/bjoc.19.80
• One‐pot regioselective synthesis of new imidazo[4,5‐<i>e</i>]thiazolo[3,2‐<i>b</i>][1,2,4]triazines by reaction of imidazotriazines with propargyl bromide
  作者：Ekaterina E. Vinogradova、Angelina N. Kravchenko、Galina A. Gazieva

  DOI：10.1002/jhet.4706

  日期：2023.9

  A regioselective one-pot method for the synthesis of imidazo[4,5-e]thiazolo[3,2-b][1,2,4]triazine derivatives has been developed by the reaction of imidazotriazinethiones with propargyl bromides upon treatment with potassium carbonate in methanol. The synthesis was accomplished by converting the imidazotriazinethiones into S-propargyl derivatives followed by subsequent 5-exo-dig cyclization. The mechanism

  通过咪唑三嗪硫酮与炔丙基溴在钾处理下反应，开发了一种区域选择性合成咪唑并[4,5- e ]噻唑并[3,2- b ][1,2,4]三嗪衍生物的方法甲醇中的碳酸盐。通过将咪唑三嗪硫酮转化为S-炔丙基衍生物，随后进行5-exo-dig环化来完成合成。使用氘标记研究环化机制。
• Regioselective synthesis of new imidazo[4,5‐<i>e</i>][1,3]thiazino[2,3‐<i>c</i>][1,2,4]triazines via reaction of imidazo[4,5‐<i>e</i>][1,2,4]triazinethiones with ethyl phenylpropiolate
  作者：Dmitry B. Vinogradov、Alexei N. Izmest'ev、Angelina N. Kravchenko、Natalya G. Kolotyrkina、Galina A. Gazieva

  DOI：10.1002/jhet.4753

  日期：2024.1

  been developed by the reaction of imidazotriazinethiones with ethyl phenylpropiolate upon treatment with potassium carbonate or sodium methoxide in methanol. The synthesis was accomplished by Michael-type addition of the imidazotriazinethiones to the triple bond of ethyl phenylpropiolate followed by subsequent intramolecular cyclization.

  通过咪唑三嗪硫酮与苯丙炔酸乙酯反应，建立了咪唑并[4,5- e ][1,3]噻嗪[2,3- c ][1,2,4]三嗪衍生物的区域选择性合成方法。与碳酸钾或甲醇钠在甲醇中反应。该合成是通过将咪唑三嗪硫酮类迈克尔型加成到苯基丙炔酸乙酯的三键上，然后进行分子内环化来完成的。