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 55 条
  • [1] 1,2,3-TRIAZOLE-[2',5'-BIS-O-(TERT-BUTYLDIMETHYLSILYL)-BETA-D-RIBOFURANOSYL]-3'-SPIRO-5''-(4''-AMINO-1'',2''-OXATHIOL 2'',2''-DIOXIDE) (TSAO) ANALOGS - SYNTHESIS AND ANTI-HIV-1 ACTIVITY
    ALVAREZ, R
    VELAZQUEZ, S
    SANFELIX, A
    AQUARO, S
    DECLERCQ, E
    PERNO, CF
    KARLSSON, A
    BALZARINI, J
    CAMARASA, MJ
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (24) : 4185 - 4194
  • [2] Diversified Synthesis of 2-(4-Oxo[1,2,3]triazolo[1,5-a]quinoxalin-5(4H)-yl)acetamide Derivatives through Ugi-4-CR and Copper-Catalyzed Tandem Reactions
    An, Yu
    He, Huan
    Liu, Tiantian
    Zhang, Yong
    Lu, Xiaoyun
    Cai, Qian
    [J]. SYNTHESIS-STUTTGART, 2017, 49 (17): : 3863 - 3873
  • [3] Banfi L, 2010, TOP HETEROCYCL CHEM, V23, P1, DOI 10.1007/7081_2009_23
  • [4] 1,2,3-triazolo[1,5-a]quinoxalines: synthesis and binding to benzodiazepine and adenosine receptors
    Bertelli, L
    Biagi, G
    Giorgi, I
    Manera, C
    Livi, O
    Scartoni, V
    Betti, L
    Giannaccini, G
    Trincavelli, L
    Barili, PL
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1998, 33 (02) : 113 - 122
  • [5] New 1,2,3-triazolo[1,5-a]quinoxalines: synthesis and binding to benzodiazepine and adenosine receptors. II
    Biagi, G
    Giorgi, I
    Livi, O
    Scartoni, V
    Betti, L
    Giannacini, G
    Trincavelli, ML
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2002, 37 (07) : 565 - 571
  • [6] gem-Disubstituent Effect in Rate Acceleration of Intramolecular Alkyne-Azide Cycloaddition Reaction
    Chavan, Shrawan R.
    Gavale, Kishor S.
    Kamble, Kirtee M.
    Pingale, Subhash S.
    Dhavale, Dilip D.
    [J]. TETRAHEDRON, 2017, 73 (04) : 365 - 372
  • [7] Ugi/Himbert Arene/Allene Diels-Alder Cycloaddition to Synthesize Strained Polycyclic Skeleton
    Cheng, Guangsheng
    He, Xiang
    Tian, Lumin
    Chen, Jiawen
    Li, Chunju
    Jia, Xueshun
    Li, Jian
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (21) : 11100 - 11107
  • [8] Recent developments in isocyanide based multicomponent reactions in applied chemistry
    Dömling, A
    [J]. CHEMICAL REVIEWS, 2006, 106 (01) : 17 - 89
  • [9] Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO
  • [10] 2-U