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
  • [21] A novel three-component one-pot synthesis of 1H-imidazol-4-yl-pyridines
    Illgen, K
    Nerdinger, S
    Behnke, D
    Friedrich, C
    ORGANIC LETTERS, 2005, 7 (01) : 39 - 42
  • [22] A convenient method for the synthesis of 7-amino-substituted 1,2,4-triazolo[1,5-a][1,3,5]triazin-5-amines
    Dolzhenko, Anton V.
    Pastorin, Giorgia
    Dolzhenko, Anna V.
    Chui, Wai Keung
    TETRAHEDRON LETTERS, 2008, 49 (50) : 7180 - 7183
  • [23] Microwave-assisted one-pot three component synthesis of some new 4(3H)-quinazolinone derivatives
    Dabiri, M
    Salehi, P
    Khajavi, MS
    Mohammadi, AA
    HETEROCYCLES, 2004, 63 (06) : 1417 - 1421
  • [24] FeCl3-SiO2 promoted one-pot, three-component synthesis of novel 1,5-benzodiazepine derivatives
    An, Ying-Shuang
    Li, Xiao-Qing
    An, Xiao-Ran
    Wang, Lan-Zhi
    MONATSHEFTE FUR CHEMIE, 2015, 146 (01): : 165 - 172
  • [25] A Novel One-Pot, Three-Component Synthesis of Dialkyl 5-(Alkylamino)-1-aryl-1H-pyrazole-3,4-dicarboxylates
    Adib, Mehdi
    Mohammadi, Bagher
    Bijanzadeh, Hamid Reza
    SYNLETT, 2008, (20) : 3180 - 3182
  • [26] Ceric ammonium nitrate catalyzed one-pot three-component microwave-assisted synthesis of indole-substituted fused pyrimidine and pyridine derivatives
    Anjirwala, Sharmil N.
    Patel, Saurabh K.
    TETRAHEDRON, 2024, 155
  • [27] Solvent-Free Microwave-Assisted Synthesis of Novel 4-Hetarylpyrazolo[1,5-a][1,3,5]triazines
    Insuasty, Henry
    Estrada, Sandra
    Quiroga, Jairo
    Insuasty, Braulio
    Abonia, Rodrigo
    Nogueras, Manuel
    Cobo, Justo
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2012, 49 (06) : 1339 - 1345
  • [28] An efficient, one-pot three-component synthesis of 4H-thiazolo[3,2-a][1,3,5]triazin-6-one derivatives
    Ubeid, Mustafa T.
    Thabet, Hamdy K.
    El-Feky, Said A.
    HETEROCYCLIC COMMUNICATIONS, 2016, 22 (01) : 43 - 47
  • [29] Microwave-Assisted One-Pot Synthesis of Substituted 3-Bromoimidazo [1,2-a]pyridines and Imidazoheterocycles
    Patil, Shashikant M.
    Mascarenhas, Malcolm
    Sharma, Rajiv
    Roopan, S. Mohana
    Roychowdhury, Abhijit
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2014, 51 (05) : 1509 - 1515
  • [30] CONVENIENT ONE-POT SYNTHESIS OF 5-(SUBSTITUTED AMINO)-1,2,3,4-THIATRIAZOLES
    Katritzky, Alan R.
    Meher, Geeta
    Narindoshvili, Tamari
    COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 2009, 74 (7-8) : 1061 - 1068