One-Pot Synthesis of [1,2,3]Triazolo[1,5-a]quinoxalin-4(5H)-ones by a Metal-Free Sequential Ugi-4CR/Alkyne-Azide Cycloaddition Reaction

被引:12
|
作者
Yan, Yan-Mei [1 ]
Li, Hao-Yang [1 ]
Zhang, Min [1 ]
Wang, Rong-Xin [1 ]
Zhou, Chen-Guang [1 ]
Ren, Zhen-Xing [2 ]
Ding, Ming-Wu [3 ]
机构
[1] Taiyuan Normal Univ, Dept Chem, Jinzhong 030619, Peoples R China
[2] Shanxi Univ, Inst Appl Chem, Taiyuan 030006, Shanxi, Peoples R China
[3] Cent China Normal Univ, Wuhan 430079, Hubei, Peoples R China
基金
中国国家自然科学基金;
关键词
one-pot; metal-free; 1,2,3]triazolo[1,5,a]quinoxalin-4(5H)-one; Ugi reaction; alkyne-azide cycloaddition reaction; MULTICOMPONENT REACTIONS; CLICK CHEMISTRY; UGI REACTION; BENZODIAZEPINE; HETEROCYCLES; STRATEGY; INDOLES; CONCISE; BIOLOGY; BINDING;
D O I
10.1055/s-0037-1610737
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convenient and one-pot approach to prepare [1,2,3]triazolo[1,5-a]quinoxalin-4(5H)-ones by a metal-free sequential Ugi-4CR/alkyne-azide cycloaddition reaction has been developed. The reaction of 2-azidobenzenamines, aldehydes, propiolic acids, and isocyanides produced the Ugi adducts, which were transformed to the [1,2,3]triazolo[1,5- a ]quinoxalin-4(5 H )-ones in moderate to good yields via alkyne-azide cycloaddition reaction.
引用
收藏
页码:73 / 76
页数:4
相关论文
共 50 条
  • [1] One-Pot Metal-Free Synthesis of [1,2,3]triazolo[1,5-a]quinoxalines by Sequential Ugi-3CR/Alkyne-Azide Cycloaddition Reaction
    Shi, Ying
    Qin, Fuwen
    Wang, Jie
    Yan, Yanmei
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (01) : 297 - 302
  • [2] Synthesis of pyrazolo[1,5-a] quinoxalin-4(5H)-ones via one-pot amidation/N-arylation reactions under transition metal-free conditions
    Wiethan, Carson
    Franceschini, Steffany Z.
    Bonacorso, Helio G.
    Stradiotto, Mark
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (37) : 8721 - 8727
  • [3] Rejuvenating the [1,2,3]-triazolo [1,5-a]quinoxalin-4(5H)-one scaffold: Synthesis and derivatization in a sustainable guise and preliminary antimicrobial evaluation
    Pelliccia, Sveva
    Alfano, Antonella Ilenia
    Gomes Da Assuncao, Beatriz Ramos
    Turco, Luigia
    Lembo, Francesca
    Summa, Vincenzo
    Buommino, Elisabetta
    Brindisi, Margherita
    FRONTIERS IN CHEMISTRY, 2023, 11
  • [4] Synthesis of [1,2,3]Triazolo[1,5-a]quinoxalin-4(5H)-ones through Copper-Catalyzed Tandem Reactions of N-(2-Haloaryl)propiolamides with Sodium Azide
    Yan, Jiajie
    Zhou, Fengtao
    Qin, Dongguang
    Cai, Tong
    Ding, Ke
    Cai, Qian
    ORGANIC LETTERS, 2012, 14 (05) : 1262 - 1265
  • [5] [3+2] Cyclization of Azidotrimethylsilane with Quinoxalin-2(1H)-Ones to Synthesize Tetrazolo[1,5-a]quinoxalin-4(5H)-Ones
    Yang, Qiming
    Zhang, Yuecheng
    Sun, Qian
    Shang, Kun
    Zhang, Hong-Yu
    Zhao, Jiquan
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (23) : 4509 - 4514
  • [6] One-pot synthesis of 3,4-dihydroisoquinolin-1(2H)-ones via a sequential Ugi-4CR and nucleophilic substitution reaction
    Pan, Hong-Ling
    Kong, Han-Han
    Ding, Ming-Wu
    TETRAHEDRON, 2025, 178
  • [7] Synthesis of [1,2,3]Triazolo-[1,5-a]quinoxalin-4(5H)-ones through Photoredox-Catalyzed [3+2] Cyclization Reactions with Hypervalent lodine(III) Reagents
    Wen, Jinxia
    Zhao, Wenyan
    Gao, Xu
    Ren, Xiaofang
    Dong, Chunping
    Wang, Cheli
    Liu, Li
    Li, Jian
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (06): : 4415 - 4423
  • [8] SYNTHESIS OF [1,2,3]TRIAZOLO[1,5-A][4,1]BENZOXAZEPINE VIA INTRAMOLECULAR AZIDE CYCLOADDITION
    GARANTI, L
    MOLTENI, G
    ZECCHI, G
    HETEROCYCLES, 1994, 38 (02) : 291 - 296
  • [9] Synthesis of imidazo[1,5-a]quinoxalin-4(5H)-one template via a novel intramolecular cyclization process
    Norris, D
    Chen, P
    Barrish, JC
    Das, J
    Moquin, R
    Chen, BC
    Guo, P
    TETRAHEDRON LETTERS, 2001, 42 (26) : 4297 - 4299
  • [10] Metal-Free Intramolecular Alkyne-Azide Cycloaddition To Construct the Pyrazolo[4,3-f][1,2,3]triazolo[5,1-c][1,4]oxazepine Ring System
    Arbaciauskiene, Egle
    Laukaityte, Vaida
    Holzer, Wolfgang
    Sackus, Algirdas
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (25) : 5663 - 5670