Synthesis of 1,5-disubstituted tetrazole-1,2,3 triazoles hybrids via Ugi-azide/CuAAC

被引：15
|
作者：
Aguilar-Morales, Cesia M. [1 ]
de Loera, Denisse [2 ]
Contreras-Celedon, Claudia [1 ]
Cortes-Garcia, Carlos J. [1 ]
Chacon-Garcia, Luis [1 ]
机构：
[1] Univ Michoacana, Inst Invest Quim Biol, Lab Diseno Mol, Ciudad Univ, Morelia 58033, Michoacan, Mexico
[2] Univ Autonoma San Luis Potosi, Fac Ciencias Quim, San Luis Potosi, Mexico
来源：
SYNTHETIC COMMUNICATIONS | 2019年 / 49卷 / 16期
关键词：
1,5-Disubstituted tetrazole; 1,4-disubstituted-1,2,3-triazoles; hybrids compounds; multicomponent reaction; Ugi-azide; CARBOXYLIC-ACID ISOSTERES; CLICK CHEMISTRY; MULTICOMPONENT REACTIONS; MEDICINAL CHEMISTRY; AZIDE; CYCLOADDITION; 1,2,3-TRIAZOLES; HYBRIDIZATION; DERIVATIVES; INHIBITORS;
D O I：
10.1080/00397911.2019.1616301
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new synthetic strategy to obtain new linked 1,5-disubstituted tetrazole-1,2,3-triazoles via the Ugi-azide reaction followed by a copper-catalyzed alkyne-azide reaction (CuAAC) was developed. This strategy used solvent-free conditions for the Ugi-azide reaction. This two-step strategy affords the products in moderate to good yields. To the best of our knowledge, this is the first report using the CuAAC reaction as a post-condensation process in an Ugi-azide reaction and therefore, the first describing the synthesis of 1,5-disubstituted tetrazole (1,5-DS-T) linked to the 1,2,3-triazole moiety, which are molecules that may have potential applications in medicinal chemistry. [GRAPHICS]
引用
收藏
页码：2086 / 2095
页数：10
相关论文
共 50 条
  • [31] Are 1,4-and 1,5-Disubstituted 1,2,3-Triazoles Good Pharmacophoric Groups?
    Massarotti, Alberto
    Aprile, Silvio
    Mercalli, Valentina
    Del Grosso, Erika
    Grosa, Giorgio
    Sorba, Giovanni
    Tron, Gian Cesare
    CHEMMEDCHEM, 2014, 9 (11) : 2497 - 2508
  • [32] REGIOSELECTIVE SYNTHESIS OF 1,5-DISUBSTITUTED 1,2,3-TRIAZOLES BY REUSABLE AlCl3 IMMOBILIZED ON γ-Al2O3
    Nanjundaswamy, Hemmaragala M.
    Abrahamse, Heidi
    SYNTHETIC COMMUNICATIONS, 2015, 45 (08) : 967 - 974
  • [33] A Metal-Free Multicomponent Cascade Reaction for the Regiospecific Synthesis of 1,5-Disubstituted 1,2,3-Triazoles
    Cheng, Guolin
    Zeng, Xiaobao
    Shen, Jinhai
    Wang, Xuesong
    Cui, Xiuling
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (50) : 13265 - 13268
  • [34] Light-Triggered Nickel-Catalyzed Azide-Alkyne Cycloaddition for the Preparation of 1,5-Disubstituted 1,2,3-Triazoles
    Abadie, Baptiste
    Almansa, Axel
    He, Ouchan
    Massip, Stephane
    Molton, Florian
    Duboc, Carole
    Vincent, Jean-Marc
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (24) : 4266 - 4270
  • [35] Synthesis of 1,5-Disubstituted 1H-Tetrazole Derivatives via a Three-Component Reaction of Carbodiimides, Isocyanides, and Trimethylsilyl Azide
    Kazemizadeh, Ali Reza
    Hajaliakbari, Nasrin
    Hajian, Roghayeh
    Shajari, Nahid
    Ramazani, Ali
    HELVETICA CHIMICA ACTA, 2012, 95 (04) : 594 - 597
  • [36] Combining the Ugi-azide multicomponent reaction and rhodium(III)-catalyzed annulation for the synthesis of tetrazole-isoquinolone/pyridone hybrids
    Ojeda, Gerardo M.
    Ranjan, Prabhat
    Fedoseev, Pavel
    Amable, Lisandra
    Sharma, Upendra K.
    Rivera, Daniel G.
    Van der Eycken, Erik V.
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2019, 15 : 2447 - 2457
  • [37] Chiral 1,5-disubstituted 1,2,3-triazoles - versatile tools for foldamers and peptidomimetic applications
    Stalsmeden, Anna Said
    Paterson, Andrew J.
    Szigyarto, Imola Cs
    Thunberg, Linda
    Johansson, Johan R.
    Beke-Somfai, Tamas
    Kann, Nina
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (10) : 1957 - 1967
  • [38] Ce(OTf)3-Catalyzed [3+2] Cycloaddition of Azides with Nitroolefins: Regioselective Synthesis of 1,5-Disubstituted 1,2,3-Triazoles
    Wang, Ying-Chun
    Xie, Yu-Yang
    Qu, Hong-En
    Wang, Heng-Shan
    Pan, Ying-Ming
    Huang, Fu-Ping
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (10): : 4463 - 4469
  • [39] SYNTHESIS OF N-ALKYL SUBSTITUTED AZASUGAR-TETRAZOLE HYBRID MOLECULES VIA UGI-AZIDE REACTION
    Luo, Hairong
    Xu, Bangjian
    Zhang, Lingyu
    Chen, Meihang
    HETEROCYCLES, 2019, 98 (04) : 544 - 550
  • [40] Enzyme-Catalyzed Regioselective Synthesis of 4-Hetero-Functionalized 1,5-Disubstituted 1,2,3-Triazoles
    Kumar, Navaneet
    Kumar, Atul
    ORGANIC LETTERS, 2024, 26 (36) : 7514 - 7519
12345