A transition-metal-free azide-alkyne cycloaddition/hydroamination cascade reaction for the construction of triazole-fused piperazin-2-ones

被引：0
|
作者：
Qiu, Kongxi [1 ]
Wu, Kaifu [1 ]
Ma, Haowen [1 ]
Ao, Yunlin [1 ]
Zhou, Wei [1 ]
Cai, Qian [1 ]
机构：
[1] Jinan Univ, Coll Pharm, 601 Huangpu Ave West, Guangzhou 510632, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2024年 / 22卷 / 06期
基金：
中国国家自然科学基金;
关键词：
CLICK CHEMISTRY; CYCLOADDITION; HETEROCYCLES; PHASE;
D O I：
10.1039/d3ob01999c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A time-dependent, divergent synthesis of highly functionalized [1,2,3]triazolo[1,5-a]pyrazin-4(5H)-one (reaction time: 12 h) or 6,7-dihydro-[1,2,3]triazolo[1,5-a]pyrazin-4(5H)-one (reaction time: 2 h) scaffolds via a cascade azide-alkyne cycloaddition/hydroamination protocol is reported. The transformation features good functional group compatibility, broad substrate scope, high atom economy and avoidance of the use of transition-metal catalysts. A time-dependent, divergent synthesis of [1,2,3]triazolo[1,5-a]pyrazin-4(5H)-one (reaction time: 12 h) or 6,7-dihydro-[1,2,3]triazolo[1,5-a]pyrazin-4(5H)-one (reaction time: 2 h) scaffolds is reported.
引用
收藏
页码：1176 / 1180
页数：5
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  • [1] Synthesis of Bioactive 1,2,3-Triazole-Fused Macrocycles via Azide-Alkyne Cycloaddition
    Jahan, Nasrin
    Pal, Arkadip
    Ansary, Inul
    [J]. SYNOPEN, 2024, 08 (01): : 1 - 38
  • [2] Synthesis of 1,2,3-Triazole-Fused Heterocycles via Intramolecular Azide-Alkyne Cycloaddition Reactions
    Majumdar, Krishna C.
    Ray, Krishanu
    [J]. SYNTHESIS-STUTTGART, 2011, (23): : 3767 - 3783
  • [3] Chiral Guanidine/Copper Catalyzed Asymmetric Azide-Alkyne Cycloaddition/[2+2] Cascade Reaction
    Guo, Songsong
    Dong, Pei
    Chen, Yushuang
    Feng, Xiaoming
    Li, Xiaohua
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (51) : 16852 - 16856
  • [4] Reaction mechanisms of transition-metal-catalyzed azide-alkyne cycloaddition "click" reactions: A DFT investigation
    Ikhlef, Djamila
    Wang, Changlong
    Kahlal, Samia
    Maouche, Boubekeur
    Astruc, Didier
    Saillard, Jean-Yves
    [J]. COMPUTATIONAL AND THEORETICAL CHEMISTRY, 2015, 1073 : 131 - 138
  • [5] Traceless Tosylhydrazone-Based Triazole Formation: A Metal-Free Alternative to Strain-Promoted Azide-Alkyne Cycloaddition
    van Berkel, Sander S.
    Brauch, Sebastian
    Gabriel, Lars
    Henze, Michael
    Stark, Sebastian
    Vasilev, Dimitar
    Wessjohann, Ludger A.
    Abbas, Muhammad
    Westermann, Bernhard
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (22) : 5343 - 5346
  • [6] Metal-Free 1,5-Regioselective Azide-Alkyne [3+2]-Cycloaddition
    Kloss, Florian
    Koehn, Uwe
    Jahn, Burkhard O.
    Hager, Martin D.
    Goerls, Helmar
    Schubert, Ulrich S.
    [J]. CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (10) : 2816 - 2824
  • [7] ACID PROMOTED METAL FREE SYNTHESIS OF TRIAZOLE-FUSED HETEROCYCLES VIA INTRAMOLECULAR [3+2] CYCLOADDITION
    Zhang, Youlai
    Wang, Mengdi
    Li, Junru
    Di, Qingtong
    Tian, Ziye
    Chen, Baoquan
    Zhang, Huan
    Tanimoto, Hiroki
    Morimoto, Tsumoru
    Kakiuchi, Kiyomi
    [J]. HETEROCYCLES, 2018, 96 (05) : 947 - 957
  • [8] Theoretical Study on Cooperation Catalysis of Chiral Guanidine/ Copper(I) in Asymmetric Azide-Alkyne Cycloaddition/[2+2] Cascade Reaction
    Wei, Qi
    Zhang, Yan
    Lv, Cidan
    Hu, Changwei
    Su, Zhishan
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (14): : 9973 - 9986
  • [9] Metal-Free Tandem Approach for Triazole-Fused Diazepinone Scaffolds via [3+2]Cycloaddition/C-N Coupling Reaction
    Majeed, Kashif
    Wang, Lingna
    Liu, Bangjie
    Guo, Zijian
    Zhou, Fengtao
    Zhang, Qiuyu
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (01): : 207 - 222
  • [10] Intramolecular Azide-Alkyne [3+2] Cycloaddition: A Versatile Route for the Synthesis of 1,2,3-Triazole Fused Dibenzo[1,5]diazocine Derivatives
    Majumdar, K. C.
    Ray, Krishanu
    Ganai, Sintu
    [J]. SYNTHESIS-STUTTGART, 2010, (12): : 2101 - 2105
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