3,4-diamino-5-methyl-1,2,4-triazole hydrochloride | 73214-26-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3,4-diamino-5-methyl-1,2,4-triazole hydrochloride
• 英文别名: 4,5-diamino-3-methyl-4H-1,2,4-triazol-1-ium chloride；4,5-Diamino3-methyl-4h-1,2,4-triazol-1-ium chloride；5-methyl-1H-1,2,4-triazol-4-ium-3,4-diamine;chloride
• CAS: 73214-26-3
• 化学式: C₃H₇N₅*ClH
• 分子量: 149.583
• InChiKey: SUJJGEDIBAYWOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  82.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-diamino-5-methyl-1,2,4-triazole hydrochloride 在 silver nitrate 作用下， 以 乙醇 、 水 为溶剂， 反应 6.0h， 以70%的产率得到4,5-diamino-3-methyl-4H-1,2,4-triazol-1-ium nitrate
  参考文献：
  名称：

  新型三唑鎓盐的合成、表征、晶体结构和热行为以及对接研究

  摘要：

  合成了一种新型三唑类化合物4,5-二氨基-3-甲基-4H-1,2,4-三唑-1-鎓硝酸盐(DAMT·HNO3)，并通过元素分析、FTIR、1H NMR光谱和单晶表征X 射线衍射和热分析 (TGA/DSC)。该化合物的 X 射线分析揭示了具有新互变异构形式的硝酸三唑鎓盐。在不同的 NH…X 键 (X = C, N, O) 中，NH…O 键形成 R22(4)、R24(8)、R44(18)、R42(14) 和 R12(4) 氢键基序. DAMT·HNO3 的晶体网络也通过三唑环之间的π-π 堆积相互作用而稳定。热学研究表明，该化合物具有良好的热稳定性，并且可以在第一次分解步骤中释放出大量的热量。此外，将该化合物的热性能与其氯化物盐类似物 DAMT·HCl 进行了比较。通过DFT计算研究了DAMT·HNO3的热力学稳定性，并与DAMT·HCl和DAMT的热力学稳定性进行了比较。通过对接研究来研究这些化合物与

  DOI：

  10.1134/s002247662003004x
• 作为产物：
  描述：

  1,3-二氨基胍盐酸盐 、 溶剂黄146 反应 24.0h， 以78%的产率得到3,4-diamino-5-methyl-1,2,4-triazole hydrochloride
  参考文献：
  名称：

  Synthesis, characterization, and crystal structure of a tricadmium complex of 3,4-diamino-5-methyl-1,2,4-triazole

  摘要：

  The ligand 3,4-diamino-5-methyl-4H-1,2,4-triazole (DAMT) and its trinuclear cadmium complex [Cd3(DAMT)2(DAMTH)2Cl8] have been prepared and identified by elemental analyses, infrared, Raman, 1H and 13C NMR spectroscopy, and single crystal X-ray diffraction. The protonation equilibria of the ligand have been studied by pH-potentiometry, with pK1 13.29 and pK2 5.40 determined. The free ligand consists of triazole cations (DAMTH) and chloride counter ions. The neutral cadmium compound is a complex of the cationic ligand in which three Cd's are coordinated by two unidentate cation forms of the ligands (DAMTH), two ambidentate neutral forms of the ligand (DAMT), and eight chlorides. Cadmium ions have slightly distorted octahedral geometry.

  DOI：

  10.1080/00958972.2010.537331

文献信息

• Synthesis of 3-(Alditol-1-yl)triazolo[4′,3′:2,3]-1,2,4-triazino[5,6-<i>b</i>]indoles
  作者：Ahmed Mousaad、Hamida Abdel Hamid、Ahmed El Nemr、El Sayed H. El Ashry

  DOI：10.1246/bcsj.65.546

  日期：1992.2

  A series of the hydrazones were prepared by the reaction of 3-hydrazino-5H-1,2,4-triazino[5,6-b]indole (1) with monosaccharides, and their acetylation was studied. Cyclodehydrogenation of the hydrazones gave 3-(substituted)-10H-1,2,4-triazolo[4′,3′:2,3][1,2,4]triazino[5,6-b]indole, whose acetylation and partial acetylation were carried out. The ring-chain tautomerism of the hydrazones promoted their

  3-肼基-5H-1,2,4-三嗪基[5,6-b]吲哚(1)与单糖反应制备了一系列腙，并对其乙酰化进行了研究。腙环脱氢得到 3-(取代)-10H-1,2,4-三唑并[4',3':2,3][1,2,4]三嗪基[5,6-b]吲哚，其乙酰化并进行部分乙酰化。腙的环链互变异构促进了它们的杂环化。产品选择了线性结构，而不是有角异构体的结构。该结构已从 1 的乙醛衍生物环化的模型研究中得到证实，发现其与 4,5-二氨基-3-甲基-1,2,4-三唑反应所得产物相同与靛红。还研究了腙及其环化产物的高碘酸盐氧化。
• Regioisomeric Formation of Acenaphtho[1,2-<i>e</i>][1,2,4]triazolo[3,4-<i>c</i>][1,2,4]triazines and Their Acyclic C-Nucleoside Analogues
  作者：Nagwa Rashed、Mahmoud Shoukry、El Sayed H. El Ashry

  DOI：10.1246/bcsj.67.149

  日期：1994.1

  The oxidative cyclization of the ethylidene derivative of 3-hydrazinoacenaphtho[1,2-e][1,2,4]triazine (2) gave regioselectively the angular isomer 1-methylacenaphtho[1,2-e][1,2,4]triazolo[3,4-c][1,2,4]triazine (5). Its linear isomer 10-methylacenaphtho[1,2-e][1,2,4]triazolo[4,3-b][1,2,4]triazine (4) was synthesized by the condensation of acenaphthenequinone (6) with 3,4-diamino-5-methyl-4H-1,2,4-triazole. Condensation of 2 with a number of monosaccharides afforded the respective hydrazones 9 whose oxidative cyclization gave the corresponding 1-(polyhydroxyalkyl)acenaphtho[1,2-e][1,2,4]triazolo[3,4-c][1,2,4]triazine (10). Acetylation of 9 and 10 gave 3-[N-acetyl-N′-(polyacetoxyalkylidene)hydrazino]acenaphtho[1,2-e][1,2,4]triazine (11) and 1-(polyacetoxyalkyl)acenaphtho[1,2-e][1,2,4]triazolo[3,4-c][1,2,4]triazine (13) respectively. Periodate oxidation of 9e gave 3-(2-oxoethylidenehydrazino)acenaphtho[1,2-e][1,2,4]triazine (14).

  氧化环化3-肼基苊并[1,2-e][1,2,4]三嗪的乙叉衍生物(2),区域选择性地得到了角状异构体1-甲基苊并[1,2-e][1,2,4]三唑并[3,4-c][1,2,4]三嗪(5)。其线性异构体10-甲基苊并[1,2-e][1,2,4]三唑并[4,3-b][1,2,4]三嗪(4)通过苊醌(6)与3,4-二氨基-5-甲基-4H-1,2,4-三唑的缩合反应合成。(2)与多种单糖的缩合反应得到相应脎(9),其氧化环化反应得到了相应的1-(多羟基烷基)苊并[1,2-e][1,2,4]三唑并[3,4-c][1,2,4]三嗪(10)。(9)和(10)的乙酰化反应分别得到3-[N-乙酰基-N′-(多乙酸氧基亚烷基)肼基]苊并[1,2-e][1,2,4]三嗪(11)和1-(多乙酸氧基烷基)苊并[1,2-e][1,2,4]三唑并[3,4-c][1,2,4]三嗪(13)。(9e)的过碘酸氧化反应得到3-(2-氧代亚乙基肼基)苊并[1,2-e][1,2,4]三嗪(14)。
• Acyclo C-Nucleosides Analogues of Condensed 1,2,4-Triazines
  作者：El Sayed H. El Ashry、Nagwa Rashed、Hamida Abdel Hamid、El Sayed Ramadan

  DOI：10.1515/znb-1997-0717

  日期：1997.7.1

  7-methyl-10H-1,2,4-triazolo[3’,4’:3,4][1,2,4]triazino[5,6-b]indoles (9) have been prepared by cyclodehydrogenation of the sugar derivatives of 3-hydrazino-8-methyl-5H-1,2,4-triazino[5,6-b]indole (1). The respective linear isomer as 4 has been prepared by a dehydrative cyclization of the amides of 1. Acetylation of the sugar hydrazones and their cyclized products gave the per-N,O-acetyl derivatives. The molecular

  摘要 7-甲基-10H-1,2,4-三唑并[3',4':3,4][1,2,4]三嗪基[5,6-b]吲哚的1-无环C-核苷 (9 ) 是通过 3-hydrazino-8-methyl-5H-1,2,4-triazino[5,6-b]indole (1) 的糖衍生物环化脱氢制备的。相应的线性异构体 4 已通过 1 的酰胺的脱水环化制备。糖腙及其环化产物的乙酰化得到全-N,O-乙酰基衍生物。产物的分子连通性是通过 1H、13C 和 2D H ,H Cozy 光谱建立的。
• Sterically controlled regiospecific heterocyclization of 3-hydrazino-5-methyl-1,2,4-triazino[5,6-b]indole to 10-methyl-1,2,4-triazolo[4′,3′:2,3]1,2,4-triazino[5,6-b]indoles
  作者：M.A.E Shaban、A.Z Nasr、A.E.A Morgaan

  DOI：10.1016/s0014-827x(99)00107-x

  日期：1999.11

  3-Hydrazino-5-methyl-1,2,4-triazino[5,6-b]indole underwent sterically controlled regiospecific heterocyclizations with a variety of one-carbon cyclizing agents to give the sterically more favored linearly annulated 10-methyl-1,2,4-triazolo[4',3':2,3[1,2,4-triazino[5,6-b]indoles rather than the sterically less favored angularly annulated 10-methyl-1,2,4-triazolo[3',4':3,4]1,2,4-triazino[5,6-b]indoles. The assigned structures

  3-Hydrazino-5-methyl-1,2,4-triazino [5,6-b]吲哚与多种单碳环化剂进行空间控制的区域特异性杂环化反应，得到空间上更有利的线性环化的10-甲基-1 ，2,4-三唑并[4'，3'：2,3 [1,2,4-三嗪并[5,6-b]吲哚，而不是在空间上较不受欢迎的角环化的10-甲基-1,2,4- triazolo [3'，4'：3,4] 1,2,4-triazino [5,6-b]吲哚。通过与明确合成的真实数据，化学和光谱数据进行比较，确定了指定的结构。研究了一些制备的化合物的抗菌活性。
• 6- AND 7-Aryl-1,2,4-triazolo[4,3-b]-1,2,4-triazines
  申请人：American Cyanamid Company

  公开号：US04159375A1

  公开（公告）日：1979-06-26

  This application discloses 6- or 7-(o-, m- or p-substituted-phenyl)-1,2,4-triazolo[4,3-b]-1,2,4-triazines useful as anxiolytic agents.

  这种应用揭示了作为抗焦虑药物有用的6-或7-(o-, m-或p-取代苯基)-1,2,4-三氮唑[4,3-b]-1,2,4-三嗪。