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

页码：1176 / 1180

页数：5

共 38 条

[1] A transition-metal-free azide-alkyne cycloaddition/oxetane ring opening cascade reaction for the construction of hydroxymethyl decorated triazole-fused piperazin-2-ones and [1,4]diazepin-4-ones
Fu, Cong
Xu, Mingjin
Ma, Qicai
Wang, Wenjing
Li, Shanyue
Zhao, Qingjie
Zhou, Wei
ORGANIC CHEMISTRY FRONTIERS, 2025,
[2] Synthesis of Bioactive 1,2,3-Triazole-Fused Macrocycles via Azide-Alkyne Cycloaddition
Jahan, Nasrin
Pal, Arkadip
Ansary, Inul
SYNOPEN, 2024, 08 (01): : 1 - 38
[3] Advancements in transition metal-catalyzed 1,2,3-triazole synthesis via azide-alkyne cycloaddition
Ullah, Arif
Wahab, Abdul
Ahmad, Sadaf
Khan, Shahab
Mukherjee, Somnath
Islam, Rehmat
Abbasi, Bakar Bin Khatab
Ismail, Mostafa A.
Bukhari, Kareem Shah
REVIEWS IN INORGANIC CHEMISTRY, 2024,
[4] Synthesis of 1,2,3-Triazole-Fused Heterocycles via Intramolecular Azide-Alkyne Cycloaddition Reactions
Majumdar, Krishna C.
Ray, Krishanu
SYNTHESIS-STUTTGART, 2011, (23): : 3767 - 3783
[5] Chiral Guanidine/Copper Catalyzed Asymmetric Azide-Alkyne Cycloaddition/[2+2] Cascade Reaction
Guo, Songsong
Dong, Pei
Chen, Yushuang
Feng, Xiaoming
Li, Xiaohua
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (51) : 16852 - 16856
[6] 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
COMPUTATIONAL AND THEORETICAL CHEMISTRY, 2015, 1073 : 131 - 138
[7] 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
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (22) : 5343 - 5346
[8] 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.
CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (10) : 2816 - 2824
[9] 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
HETEROCYCLES, 2018, 96 (05) : 947 - 957
[10] 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
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (14): : 9973 - 9986

← 1 2 3 4 →