Pd-catalyzed Suzuki/Sonogashira cross-coupling reaction and the direct sp3 arylation of 7-chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine

被引:22
|
作者
Loubidi, Mohammed [1 ]
Moutardier, Anais [1 ]
Campos, Joana F. [1 ]
Berteina-Raboin, Sabine [1 ]
机构
[1] Univ Orleans, Inst Organ & Analyt Chem, CNRS, UMR 7311, BP 6759,Rue Chartres, F-45067 Orleans 2, France
关键词
Triazolo[1,5-a]pyrimidine; Suzuki; Sonogashira; Palladium; Direct sp(3) arylation; C-C; POTENT; AGENTS; SONOGASHIRA; DESIGN; TRIAZOLOPYRIMIDINES; HETEROCYCLES; DERIVATIVES; INHIBITORS; DIVERSITY;
D O I
10.1016/j.tetlet.2018.02.001
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A rapid and efficient method is reported for the synthesis of the [1,2,4]triazolo[1,5-a]pyrimidine motif. Palladium catalyzed Suzuki and Sonogashira cross coupling reactions on 7-chloro-5-methyl-(1,2,4]triazolo[1,5-a]pyrimidine were performed. The direct sp(3) arylation of compounds resulting from the Suzuki reaction was then carried out. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1050 / 1054
页数:5
相关论文
共 45 条
  • [31] Spectral, DFT/B3LYP and molecular docking analyses on ethyl 2-(5-methyl-1,2,4-triazolo[1,5-a]pyrimidin-7-yl)pent-4-enoate
    Sert, Yusuf
    Lahmidi, Sanae
    El Hafi, Mohamed
    Gokce, Halil
    Essassi, El Mokhtar
    Ejjoumamany, Abdelaziz
    Mague, Joel T.
    JOURNAL OF MOLECULAR STRUCTURE, 2020, 1206
  • [32] A New Protocol for Catalyst-Free Regioselective Synthesis of 5,9-Dihydropyrimido[5,4-e][1,2,4]triazolo[1,5-a]pyrimidine6,8(4H,7H)-diones
    Karami, Bahador
    Farahi, Mahnaz
    Banaki, Zohreh
    SYNLETT, 2015, 26 (06) : 741 - 744
  • [33] Synthesis of New Pyrazolo[ 1,5-a]pyrimidine, Triazolo[ 4,3-a] pyrimidine Derivatives, and Thieno[ 2,3-b] pyridine Derivatives from Sodium 3-(5-Methyl-1-phenyl-1H-pyrazol-4-yl)-3-oxoprop-1-en-1-olate
    Abdelhamid, Abdou O.
    Gomha, Sobhi M.
    JOURNAL OF CHEMISTRY, 2013, 2013
  • [34] Mercury(II) complexes of 4,7-dihydro-5-methyl-7-oxo[1,2,4]triazolo[1,5a]pyrimidine. Stabilization of two chemically different metal coordination environments by hydrogen bonding assembly
    Salas, JM
    Navarro, JAR
    Romero, MA
    Quiros, M
    ANALES DE QUIMICA, 1997, 93 (01): : 55 - 59
  • [35] Ligand Effects on the Pd-Catalyzed Cross-Coupling Reaction of 3-Iodoalk-2-enoates with Propargyl/1,2-Allenylic Metallic Species: An Efficient Regiodivergent Synthesis of 2,4,5-Trienoates
    Zhao, Jinbo
    Yu, Yihua
    Ma, Shengming
    CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (01) : 74 - 80
  • [36] Cu/Pd-Catalyzed One-Pot Synthesis of 2-(1,2,3-Triazolyl)methyl-3-alkynylImidazo[1,2-a]pyridines Involving Sequential SN Reaction/[3+2] Cycloaddition/Sonogashira Coupling Reactions
    El Qami, Abdelkarim
    Jismy, Badr
    El Hakmaoui, Ahmed
    Akssira, Mohamed
    Abarbri, Mohamed
    CHEMISTRYSELECT, 2021, 6 (35): : 9415 - 9420
  • [37] Synthesis, Crystal Structure and Antiproliferative Activity of 2-(((5-(((5,7-Dimethyl-[1,2,4]triazolo-[1,5-a]pyrimidin-2-yl)thio)methyl)-4-phenyl-4H-1,2,4-triazol-3-yl)thio)methyl)-4H-chromen-4-one Methanol Solvate
    Sun Hai-Yan
    CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2014, 33 (10) : 1467 - 1471
  • [38] In vitro and in vivo antiparasital activity against Trypanosoma cruzi of three novel 5-methyl-1,2,4-triazolo[1,5-a]pyrimidin-7(4H)-one-based complexes
    Caballero, Ana B.
    Marin, Clotilde
    Rodriguez-Dieguez, Antonio
    Ramirez-Macias, Inmaculada
    Barea, Elisa
    Sanchez-Moreno, Manuel
    Salas, Juan M.
    JOURNAL OF INORGANIC BIOCHEMISTRY, 2011, 105 (06) : 770 - 776
  • [39] An integration of condensation/Ullmann-type coupling/bicyclization sequences: copper-catalyzed three-component direct synthesis of [1,2,4]triazolo[1,5-b]isoquinolin-5(1H)-ones
    Jia, Feng-Cheng
    Xu, Cheng
    Cai, Qun
    Wu, An-Xin
    CHEMICAL COMMUNICATIONS, 2014, 50 (69) : 9914 - 9916
  • [40] Regioselective Synthesis of New 2,4-(Het)aryl-3H-pyrido[1′,2′:1,5]pyrazolo[4,3-d]pyrimidines Involving Palladium-Catalyzed Cross-Coupling Reactions
    Ejjoummany, Abdelaziz
    Belaroussi, Rabia
    El Hakmaoui, Ahmed
    Akssira, Mohamed
    Guillaumet, Gerald
    Buron, Frederic
    Routier, Sylvain
    MOLECULES, 2018, 23 (11):