A one-pot, three-component, microwave-assisted synthesis of novel 7-amino-substituted 4-aminopyrazolo[1,5-α][1,3,5]triazine-8-carbonitriles

被引:24
|
作者
Lim, Felicia Phei Lin [1 ]
Luna, Giuseppe [2 ]
Dolzhenko, Anton V. [1 ,2 ]
机构
[1] Monash Univ Malaysia, Sch Pharm, Selangor Darul Ehsan 47500, Malaysia
[2] Curtin Univ, Curtin Hlth Innovat Res Inst, Sch Pharm, Perth, WA 6845, Australia
关键词
Triazine; Pyrazole; Purine isostere; Multicomponent reaction; Microwave irradiation; A(2A) RECEPTOR ANTAGONISTS; PROTEIN-COUPLED RECEPTOR; FUNCTIONAL EXPRESSION; ADENINE RECEPTORS; DESIGN; INHIBITORS; MOUSE;
D O I
10.1016/j.tetlet.2015.11.006
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of novel 7-amino-substituted pyrazolo[1,5-alpha][1,3,5]triazine-8-carbonitriles was achieved via a three-component reaction of 3-amino-substituted 5-aminopyrazole-4-carbonitriles, cyanamide and triethyl orthoformate under microwave irradiation. Under catalyst-free conditions, this three-component reaction accommodated a generous diversity of amino substituents making it ideal for the generation of compound libraries for drug discovery processes. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7016 / 7019
页数:4
相关论文
共 50 条
  • [31] One-pot three-component microwave-assisted synthesis of novel thiazolidinone derivatives containing thieno[d]pyrimidine-4-one moiety as potential antimicrobial agents
    I. H. El Azab
    Sh. H. Abdel-Hafez
    Russian Journal of Bioorganic Chemistry, 2015, 41 : 315 - 323
  • [32] One-pot three-component microwave-assisted synthesis of novel thiazolidinone derivatives containing thieno[d]pyrimidine-4-one moiety as potential antimicrobial agents
    El Azab, I. H.
    Abdel-Hafez, Sh. H.
    RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, 2015, 41 (03) : 315 - 323
  • [33] A Facile One-Pot Three-Component Synthesis of 5-(Trifluoromethyl)-4,7-dihydro-[1,2,4]-triazolo[1,5-a]pyrimidine Derivatives in Ionic Liquid
    Li Tuanjie
    Yao Changsheng
    Lei Song
    Yu Chenxia
    Tu Shujiang
    CHINESE JOURNAL OF CHEMISTRY, 2011, 29 (11) : 2427 - 2432
  • [34] 2,4,6-Trichloro[1,3,5]triazine (TCT)-catalyzed one-pot Mannich-type reaction: three component synthesis of β-amino carbonyl compounds
    Nemati, Firouzeh
    Bigdeli, Mohammad A.
    Mahdavinia, Gholam Hossein
    Kiani, Hossein
    GREEN CHEMISTRY LETTERS AND REVIEWS, 2010, 3 (02) : 89 - 92
  • [35] A facile and efficient synthesis of new polysubstituted indeno[1,2-b]pyridines via one-pot, three-component microwave-assisted reaction
    Tu, Shujiang
    Jiang, Bo
    Zhang, Junyong
    Zhang, Yan
    Jia, Runhong
    Li, Chunmei
    Zhou, Dianxiang
    Cao, Longji
    Shao, Qingqing
    SYNLETT, 2007, (03) : 480 - 484
  • [36] A novel, one-pot, three-component synthesis of 4H-pyrido[1,2-a]pyrimidines
    Adib, Mehdi
    Sayahi, Mohammad Hosein
    Nosrati, Meisam
    Zhu, Long-Guan
    TETRAHEDRON LETTERS, 2007, 48 (24) : 4195 - 4198
  • [37] FeCl3–SiO2 promoted one-pot, three-component synthesis of novel 1,5-benzodiazepine derivatives
    Ying-Shuang An
    Xiao-Qing Li
    Xiao-Ran An
    Lan-Zhi Wang
    Monatshefte für Chemie - Chemical Monthly, 2015, 146 : 165 - 172
  • [38] New One-Pot Synthesis of 1,3,5-Triazines: Three-Component Condensation, Dimroth Rearrangement, and Dehydrogenative Aromatization
    Junaid, Ahmad
    Lim, Felicia Phei Lin
    Tiekink, Edward R. T.
    Dolzhenko, Anton, V
    ACS COMBINATORIAL SCIENCE, 2019, 21 (07) : 548 - 555
  • [39] One-Pot Synthesis of Imidazole-4-Carboxylates by Microwave-Assisted 1,5-Electrocyclization of Azavinyl Azomethine Ylides
    Preti, Lisa
    Attanasi, Orazio A.
    Caselli, Emilia
    Favi, Gianfranco
    Ori, Claudia
    Davoli, Paolo
    Felluga, Fulvia
    Prati, Fabio
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (22) : 4312 - 4320
  • [40] One-pot three-component reaction for the synthesis of 1-substituted-4,5-dihydro-3-alkylidenyl-pyrrolidines
    Huang, WW
    O'Donnell, MM
    Bi, G
    Liu, JF
    Yu, LB
    Baldino, CM
    Bell, AS
    Underwood, TJ
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 227 : U208 - U208