4-(m-tolyl)-2H-1,2,3-triazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(m-tolyl)-2H-1,2,3-triazole
• 英文别名: 4-m-tolyl-1H-[1,2,3]triazole
• 化学式: C₉H₉N₃
• 分子量: 159.19
• InChiKey: XQHCBHNLRWLGQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-(m-tolyl)-1-tosyl-1H-1,2,3-triazole 在 copper(II) sulfate 作用下， 反应 5.0h， 以96%的产率得到4-(m-tolyl)-2H-1,2,3-triazole
  参考文献：
  名称：

  一种2H-1,2,3-三氮唑类化合物的绿色制备方法

  摘要：

  本发明公开了一种2H‑1,2,3‑三氮唑类化合物的绿色制备方法，以1,2,3‑三氮唑衍生物为反应原料，硫酸铜为催化剂，PEG400为反应溶剂，于60℃发生取代反应制得目标产物2H‑1,2,3‑三氮唑类化合物。本发明以廉价易得的铜盐硫酸铜为催化剂，以PEG400为绿色反应溶剂，最终制得目标产物2H‑1,2,3‑三氮唑类化合物，该方法具有反应条件绿色温和、催化剂廉价易得、操作简单、收率较高且反应底物普适性广等优点。

  公开号：

  CN111170955B

文献信息

• Direct Synthesis of 4-Aryl-1,2,3-triazoles via I₂-Promoted Cyclization under Metal- and Azide-Free Conditions
  作者：Chun Huang、Xiao Geng、Peng Zhao、You Zhou、Xiao-Xiao Yu、Li-Sheng Wang、Yan-Dong Wu、An-Xin Wu

  DOI：10.1021/acs.joc.1c01702

  日期：2021.10.1

  We herein report an iodine-mediated formal [2 + 2 + 1] cyclization of methyl ketones, p-toluenesulfonyl hydrazines, and 1-aminopyridinium iodide for preparation of 4-aryl-NH-1,2,3-triazoles under metal- and azide-free conditions. Notably, this is achieved using p-toluenesulfonyl hydrazines and 1-aminopyridinium iodide as azide surrogates, providing a novel route toNH-1,2,3-triazoles. Furthermore, this

  本文我们报告碘介导的正式[2 + 2 + 1]甲基酮，环化p甲苯磺酰肼，和1-氨基吡啶碘化物用于制备4-芳基- NH下金属-1,2,3-三唑和无叠氮化物条件。值得注意的是，这是使用对甲苯磺酰肼和碘化 1-氨基吡啶鎓作为叠氮化物替代物实现的，为NH -1,2,3-三唑提供了一条新途径。此外，这种方法提供了对吲哚胺 2,3-双加氧酶 (IDO) 的强效抑制剂的快速且实用的途径。
• A [3+2] cycloaddition-1,2-acyl migration-hydrolysis cascade for regioselective synthesis of 1,2,3-triazoles in water
  作者：Gargi Chakraborti、Tirtha Mandal、Charles Patriot Roy、Jyotirmayee Dash

  DOI：10.1039/d1cc02801d

  日期：——

  involving [3+2] cycloaddition, 1,2-acyl migration and hydrolysis produces 2H-1,2,3-triazoles via the regioselective formation of N2-carboxyalkylated triazoles. The reaction proceeds in aqueous media through intriguing reaction kinetics using a CuI–prolinamide catalyst system. Prolinamide promotes the novel organocatalytic 1,2-acyl migration as well as hydrolysis of the resulting N2-carboxyalkylated triazoles

  涉及 [3+2] 环加成、1,2-酰基迁移和水解的级联序列通过N 2 -羧基烷基化三唑的区域选择性形成产生 2 H -1,2,3-三唑。该反应在水性介质中通过使用 CuI-脯氨酰胺催化剂体系的有趣反应动力学进行。脯氨酰胺促进新型有机催化 1,2-酰基迁移以及所得N 2 -羧基烷基化三唑的水解。
• Highly N²-Selective Coupling of 1,2,3-Triazoles with Indole and Pyrrole
  作者：Jian Wen、Li-Li Zhu、Qing-Wei Bi、Zhu-Qing Shen、Xiao-Xiao Li、Xin Li、Zhen Wang、Zili Chen

  DOI：10.1002/chem.201302761

  日期：2014.1.20

  Hydrogen‐bond mediated coupling of 1,2,3‐triazoles to indoles and pyrroles results in N2 selective functionalization of the triazole moiety in moderate to excellent yields. The reaction was tolerant of un‐, mono‐ and disubstituted triazoles and was applied to synthesize tryptophan derived fluorescent amino acids.

  氢键介导的1,2,3-三唑与吲哚和吡咯的偶合导致三唑部分的N2选择性官能化，产率中等至优异。该反应可耐受未取代，单取代和双取代的三唑，可用于合成色氨酸衍生的荧光氨基酸。
• Preparation of reusable Ag-decorated graphene oxide catalysts for decarboxylative cycloaddition
  作者：Ji Dang Kim、Thiruvengadam Palani、Manian Rajesh Kumar、Sunwoo Lee、Hyun Chul Choi

  DOI：10.1039/c2jm35512d

  日期：——

  In this study, we demonstrated a noble Ag-decorated graphene oxide catalyst (GOSH-Ag) for use in the decarboxylative cycloaddition reaction. The catalyst was easily prepared by depositing Ag nanoparticles on thiolated graphene oxide (GOSH) surfaces. Transmission electron microscopy (TEM) indicated that the nanoparticles were well-dispersed and of a small, approximately 3.7 nm average size. These characteristics resulted in a high surface area, which enhanced the catalytic activity of the supported catalyst. Moreover, it was found that the aggregation of Ag catalysts was inhibited by the strong adhesion between the GOSHs and the Ag nanoparticles during the chemical reactions, thereby permitting their reuse. Indeed, the supported catalyst could easily be separated and recovered from the reaction mixture and reused several times.

  在本研究中，我们展示了一种用于脱羧环加成反应的高效银修饰氧化石墨烯催化剂（GOSH-Ag）。该催化剂通过将银纳米颗粒沉积在巯基化氧化石墨烯（GOSH）表面制备而成。透射电子显微镜（TEM）显示银纳米颗粒均匀分散且平均粒径约为3.7纳米，这种特性使其具有高比表面积，从而提高了负载催化剂的活性。此外，在化学反应过程中，GOSH与银纳米颗粒之间的强粘附作用抑制了银催化剂的团聚，从而允许其重复使用。实际上，这种负载型催化剂能够轻松地从反应混合物中分离回收并多次重复使用。
• Compounds and methods
  申请人：——

  公开号：US20030220371A1

  公开（公告）日：2003-11-27

  Compounds of this invention are non-peptide, reversible inhibitors of type 2 methionine aminopeptidase, useful in treating conditions mediated by angiogenesis, such as cancer, haemangioma, proliferative retinophathy, rheumatoid arthritis, atherosclerotic neovascularization, psoriasis, ocular neovascularization and obesity.

  本发明的化合物是非肽类、可逆的第2型蛋氨酸氨肽酶抑制剂，可用于治疗由血管生成介导的疾病，如癌症、血管瘤、增殖性视网膜病变、类风湿关节炎、动脉粥样硬化性新生血管生成、银屑病、眼部新生血管生成和肥胖症。