Synthesis of pyrazolo[1,5-a] quinoxalin-4(5H)-ones via one-pot amidation/N-arylation reactions under transition metal-free conditions

被引:12
|
作者
Wiethan, Carson [1 ]
Franceschini, Steffany Z. [1 ]
Bonacorso, Helio G. [1 ]
Stradiotto, Mark [2 ]
机构
[1] Univ Fed Santa Maria, Dept Quim, BR-97105900 Santa Maria, RS, Brazil
[2] Dalhousie Univ, Dept Chem, Halifax, NS B3H 4R2, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
CATALYST;
D O I
10.1039/c6ob01407k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient one-pot transition metal-free procedure for the synthesis of new pyrazolo[1,5-a] quinoxalin-4(5H)-ones from easily prepared 1-(2-chlorophenyl-5-ethylcarboxylate) pyrazoles and various primary alkylamines is described. The key steps involved in the synthesis of the new 5,6-fused ring system are the formation of an amide intermediate followed by an intramolecular N-arylation reaction via nucleophilic aromatic substitution.
引用
收藏
页码:8721 / 8727
页数:7
相关论文
共 50 条
  • [1] 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
    Yan, Yan-Mei
    Li, Hao-Yang
    Zhang, Min
    Wang, Rong-Xin
    Zhou, Chen-Guang
    Ren, Zhen-Xing
    Ding, Ming-Wu
    [J]. SYNLETT, 2020, 31 (01) : 73 - 76
  • [2] 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
    [J]. TETRAHEDRON LETTERS, 2001, 42 (26) : 4297 - 4299
  • [3] [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
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (23) : 4509 - 4514
  • [4] Paraformaldehyde as C1 Synthon: Electrochemical Three-Component Synthesis of Tetrahydroimidazo[1,5-a]quinoxalin-4(5H)-ones in Aqueous Ethanol
    Lu, Yu-Han
    Mu, Si-Yu
    Jiang, Jun
    Zhou, Min-Hang
    Wu, Chao
    Ji, Hong-Tao
    He, Wei-Min
    [J]. CHEMSUSCHEM, 2023, 16 (19)
  • [5] Copper-Catalyzed Oxidative [3+2]-Annulation of Quinoxalin2(1H)-one with Oxime Esters toward Functionalized Pyrazolo[1,5-a]quinoxalin-4(5H)-ones as Opioid Receptor Modulators
    Yadav, Anamika
    Yadav, Anubhav
    Tripathi, Shashank
    Dewaker, Varun
    Kant, Ruchir
    Yadav, Prem Narayan
    Srivastava, Ajay Kumar
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (11): : 7350 - 7364
  • [6] One-pot synthesis of tetrazolo[1,5-a]pyrimidines under solvent-free conditions
    Ramin Ghorbani-Vaghei
    Zahra Toghraei-Semiromi
    Mostafa Amiri
    Rahman Karimi-Nami
    [J]. Molecular Diversity, 2013, 17 : 307 - 318
  • [7] One-pot synthesis of tetrazolo[1,5-a]pyrimidines under solvent-free conditions
    Ghorbani-Vaghei, Ramin
    Toghraei-Semiromi, Zahra
    Amiri, Mostafa
    Karimi-Nami, Rahman
    [J]. MOLECULAR DIVERSITY, 2013, 17 (02) : 307 - 318
  • [8] 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
    [J]. ORGANIC LETTERS, 2012, 14 (05) : 1262 - 1265
  • [9] 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
    [J]. FRONTIERS IN CHEMISTRY, 2023, 11
  • [10] Facile and Efficient Synthesis of a New Class of Pyrazolo[1,5-a]Pyrimidine Derivatives Via One-Pot Multicomponent Reactions
    A. El-Mekabaty
    A. M. Hasel
    [J]. Chemistry of Heterocyclic Compounds, 2015, 50 : 1608 - 1615