Facile and regioselective synthesis of new fluorinated [1,2,4]-triazolo [4,3-a]pyrimidin-7(1H)-one derivatives from fluorinated alkynes

被引：7
作者：
Jismy, Badr [1 ]
Allouchi, Hassan [2 ]
Aweli, Monia [3 ]
Abarbri, Mohamed [1 ]
Allouch, Fatma [3 ]
机构：
[1] Fac Sci, Lab Physicochim Mat & Electrolytes Energie PCM2E, EA 6299, Ave Monge,Parc Grandmont, F-37200 Tours, France
[2] Fac Pharm, Synth & Isolement Mol BioAct SIMBA, Lab Chim Phys, EA 7502, 31 Ave Monge, F-37200 Tours, France
[3] Univ Sfax, Inst Super Biotechnol Sfax, Lab Chim Med & Environm, Sfax 3018, Tunisia
来源：
JOURNAL OF FLUORINE CHEMISTRY | 2020年 / 229卷
关键词：
5-amino[1,2,4]triazoles; Fluorinated alkynes; One-Pot synthesis; Regioselective; Fluorinated 1,3-disubstituted[1,2,4]-triazolo[4,3-a]pyrimidin-7(1H)-ones; BETA-KETO-ESTERS; BIOLOGICAL EVALUATION; ANTIMICROBIAL ACTIVITY; ANTIFUNGAL ACTIVITIES; DIRECT ACCESS; TRIAZOLES; 5-AMINO-1,2,4-TRIAZOLES; ANTIBACTERIAL; SAR;
D O I：
10.1016/j.jfluchem.2019.109390
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
A mild, simple and efficient method for the regioselective synthesis of 3-substituted-1-phenyl[1,2,4]-triazolo[4,3-a]pyrimidin-7(1H)-ones bearing a perfluoroalkyl group on position 5 is reported herein. The synthetic route involved a one-pot two-step Michael addition/heterocyclization reaction with 2-aminotriazoles and fluorinated alkynes as starting materials.
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页数：7
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共 74 条
  • [31] 8-Azapurines as new inhibitors of cyclin-dependent kinases
    Havlicek, L
    Fuksova, K
    Krystof, V
    Orsag, M
    Vojtesek, B
    Strnad, M
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (18) : 5399 - 5407
  • [32] The combinatorial synthesis of bicyclic privileged structures or privileged substructures
    Horton, DA
    Bourne, GT
    Smythe, ML
    [J]. CHEMICAL REVIEWS, 2003, 103 (03) : 893 - 930
  • [33] Synthesis and biological evaluation of novel steroidal[17,16-d][1,2,4]triazolo [1,5-a]pyrimidines
    Huang, Li-Hua
    Zheng, Yong-Fei
    Lu, Yong-Zheng
    Song, Chuan-Jun
    Wang, Yan-Guang
    Yu, Bin
    Liu, Hong-Min
    [J]. STEROIDS, 2012, 77 (06) : 710 - 715
  • [34] An Efficient Synthesis of New 7-Trifluoromethyl-2,5-disubstituted Pyrazolo[1,5-a]pyrimidines
    Jismy, Badr
    Allouchi, Hassan
    Guillaumet, Gerald
    Akssira, Mohamed
    Abarbri, Mohamed
    [J]. SYNTHESIS-STUTTGART, 2018, 50 (08): : 1675 - 1686
  • [35] Concise and Efficient Access to 5,7-Disubstituted Pyrazolo[1,5-a]pyrimidines by Pd-Catalyzed Sequential Arylation, Alkynylation and SNAr Reaction
    Jismy, Badr
    Guillaumet, Gerald
    Allouchi, Hassan
    Akssira, Mohamed
    Abarbri, Mohamed
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (41) : 6168 - 6178
  • [36] Jones G., 1996, FUSED 5 AND 6 MEMBER, V8
  • [37] A new flexible strategy for the synthesis of gem-difluoro-bisarylic derivatives and heterocyclic analogues
    Khalaf, Ali
    Gree, Danielle
    Abdallah, Hassan
    Jaber, Nada
    Hachem, Ali
    Gree, Rene
    [J]. TETRAHEDRON, 2011, 67 (21) : 3881 - 3886
  • [38] Synthesis and in vitro activity of novel 1,2,4-triazolo[4,3-a]pyrimidine oxazolidinone antibacterial agents
    Khera, Manoj K.
    Cliffe, Ian A.
    Mathur, Tarun
    Prakash, Om
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (10) : 2887 - 2889
  • [39] Synthesis, characterization and antitumor properties of two highly cytotoxic ruthenium(III) complexes with bulky triazolopyrimidine ligands
    Lakomska, Iwona
    Fandzloch, Marzena
    Muziol, Tadeusz
    Lis, Tadeusz
    Jezierska, Julia
    [J]. DALTON TRANSACTIONS, 2013, 42 (17) : 6219 - 6226
  • [40] Molecular structure and antitumor activity of platinum(II) complexes containing purine analogs
    Lakomska, Iwona
    [J]. INORGANICA CHIMICA ACTA, 2009, 362 (03) : 669 - 681
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