4-(4-methoxyphenyl)-5-methyl-1H-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-(4-methoxyphenyl)-5-methyl-1H-1,2,3-triazole
• 英文别名: 4-(4-methoxyphenyl)-5-methyl-2H-triazole
• 化学式: C₁₀H₁₁N₃O
• 分子量: 189.217
• InChiKey: WSILTEWWOCVRPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  50.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-methoxyphenyl)-5-methyl-1H-1,2,3-triazole 、 sodium 4-methylbenzenesulfinate 在 碘 作用下， 以 乙酸乙酯 为溶剂， 反应 12.0h， 以87%的产率得到4-(4-methoxyphenyl)-5-methyl-2-p-tosyl-2H-1,2,3-triazole
  参考文献：
  名称：

  Metal-free, highly regioselective sulfonylation of NH-1,2,3-triazoles with sodium sulfinates and thiosulfonates

  摘要：

  A convenient and metal-free protocol for the highly regioselective sulfonylation of NH-1,2,3-triazoles is described. A range of readily accessible NH-1,2,3-triazoles were sulfonylated with various aryl sulfinates in the presence of molecular iodine. The scope was extended to thiosulfonates as an efficient sulfonylating agent and nitrochromene derived triazoles were also explored for selective N-sulfonylation. A variety of synthetically viable N-2-sulfonyl triazoles were obtained in moderate to high yields with excellent regioselectivities via N-S bond construction under mild reaction conditions. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2018.04.023
• 作为产物：
  描述：

  1-(对甲氧基苯基)2-硝基丙烯 在 sodium azide 、 对甲苯磺酸 作用下， 生成 4-(4-methoxyphenyl)-5-methyl-1H-1,2,3-triazole
  参考文献：
  名称：

  Metal-free, highly regioselective sulfonylation of NH-1,2,3-triazoles with sodium sulfinates and thiosulfonates

  摘要：

  A convenient and metal-free protocol for the highly regioselective sulfonylation of NH-1,2,3-triazoles is described. A range of readily accessible NH-1,2,3-triazoles were sulfonylated with various aryl sulfinates in the presence of molecular iodine. The scope was extended to thiosulfonates as an efficient sulfonylating agent and nitrochromene derived triazoles were also explored for selective N-sulfonylation. A variety of synthetically viable N-2-sulfonyl triazoles were obtained in moderate to high yields with excellent regioselectivities via N-S bond construction under mild reaction conditions. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2018.04.023

文献信息

• Aluminium(III) Chloride-Catalyzed Three-Component Condensation of Aromatic Aldehydes, Nitroalkanes and Sodium Azide for the Synthesis of 4-Aryl-<i>NH</i>-1,2,3-triazoles
  作者：Qinquan Hu、Yi Liu、Xiaocong Deng、Yanjun Li、Yunfeng Chen

  DOI：10.1002/adsc.201600098

  日期：2016.5.19

  three‐component reaction of aromatic aldehydes, nitroalkanes, and sodium azide has been developed; this reaction sequence can be applied to a broad substrate scope and affords the corresponding 4‐aryl‐NH‐1,2,3‐triazoles in good to excellent yields. The milder reaction conditions and easier operation make this AlCl3‐catalyzed protocol more advantageous for the synthesis of 4‐aryl‐NH‐1,2,3‐triazoles.

  已经开发出了一种氯化铝（III）催化的三元芳族醛，硝基烷和叠氮化钠反应。该反应顺序可应用于广泛的底物范围，并提供相应的4-芳基-NH -1,2,3-三唑，收率良好至极佳。较温和的反应条件和更简便的操作使此AlCl 3催化方案对于合成4芳基NH -1,2,3-三唑更有利。
• Copper-Catalyzed Cross-Dehydrogenative <i>N</i>²-Coupling of <i>NH</i>-1,2,3-Triazoles with <i>N</i>,<i>N</i> -Dialkylamides: <i>N</i>-Amidoalkylation of <i>NH</i>-1,2,3-Triazoles
  作者：Xiaocong Deng、Xue Lei、Gang Nie、Lihui Jia、Yuanxiang Li、Yunfeng Chen

  DOI：10.1021/acs.joc.7b00752

  日期：2017.6.16

  An efficient copper-catalyzed C–N bond formation by N–H/C–H cross-dehydrogenative coupling (CDC) between NH-1,2,3-triazoles and N,N-dialkylamides has been developed. The method provided N-amidoalkylated 1,2,3-triazoles with moderate to high yields, and the reactions showed high N2-selectivities when 4,5-disubstituted NH-1,2,3-triazoles served as the substrates.

  已经开发了通过NH -1,2,3-三唑与N，N-二烷基酰胺之间的NH - CH / CH-H交叉脱氢偶联（CDC）形成有效的铜催化C-N键的方法。该方法提供了中等至高产率的N-酰胺基烷基化的1,2,3-三唑，并且当以4,5-二取代的NH -1,2,3-三唑为底物时，反应显示出高的N 2-选择性。
• Copper(I)‐Catalyzed Regioselective Chan‐Lam <i>N</i> 2‐Vinylation of 1,2,3‐Triazoles and Tetrazoles
  作者：Vladimir Motornov、Gennadij V. Latyshev、Yury N. Kotovshchikov、Nikolay V. Lukashev、Irina P. Beletskaya

  DOI：10.1002/adsc.201900225

  日期：2019.7.11

  NH‐azoles with vinylboronic acids or vinyltrifluoroborate salt provides a direct route to N2‐vinyl‐1,2,3‐triazoles and N2‐vinyltetrazoles. The coupling reaction is efficiently catalyzed by (phen)Cu(PPh3)Br with low catalyst loading (5 mol%) under base‐free conditions. The method is applicable for vinylation of unsubstituted, monosubstituted, and disubstituted 1,2,3‐triazoles with various functionalities

  铜催化的π不足的NH-唑类与乙烯基硼酸或乙烯基三氟硼酸盐的偶联提供了直接通往N2-乙烯基1,2,3-三唑和N2-乙烯基四唑的途径。（phen）Cu（PPh 3）Br在无碱条件下以低催化剂负载量（5 mol％）有效地催化了偶联反应。该方法适用于具有高N2选择性的各种功能的未取代，单取代和二取代的1,2,3-三唑的乙烯基化。
• 一种NH-1,2,3-三唑化合物的合成方法
  申请人：武汉工程大学

  公开号：CN105669569B

  公开（公告）日：2017-12-12

  本发明涉及一种NH‑1,2,3‑三唑化合物的合成方法，属于有机及药物合成技术领域。在Lewis酸催化剂的催化下，采用芳醛、硝基烃类与叠氮化钠一锅法制备而成。本发明的有益效果是：本发明采用廉价易得的AlCl3等Lewis酸作为催化剂，芳醛，含α氢的硝基烃类化合物(其种烃为C1‑C6的烷基、C1‑C6的烷氧基或甲酸乙酯基)、叠氮化钠一锅法反应，反应条件温和，产率高，原料易得，方便有效的合成了NH‑1,2,3‑三唑化合物，与已有的方法相比，本发明所述的反应条件温和、反应时间短、安全性好、操作简便、底物范围广、反应效率高且催化剂低廉，是一种具有潜在应用价值的方法。
• Metal-free, highly regioselective sulfonylation of NH-1,2,3-triazoles with sodium sulfinates and thiosulfonates
  作者：Raju Jannapu Reddy、Angothu Shankar、Md. Waheed、Jagadeesh Babu Nanubolu

  DOI：10.1016/j.tetlet.2018.04.023

  日期：2018.5

  A convenient and metal-free protocol for the highly regioselective sulfonylation of NH-1,2,3-triazoles is described. A range of readily accessible NH-1,2,3-triazoles were sulfonylated with various aryl sulfinates in the presence of molecular iodine. The scope was extended to thiosulfonates as an efficient sulfonylating agent and nitrochromene derived triazoles were also explored for selective N-sulfonylation. A variety of synthetically viable N-2-sulfonyl triazoles were obtained in moderate to high yields with excellent regioselectivities via N-S bond construction under mild reaction conditions. (C) 2018 Elsevier Ltd. All rights reserved.