Combining click-multicomponent reaction: one-pot synthesis of triazolyl methoxy-phenyl indazolo[2,1-b]phthalazine-trione derivatives

被引:19
作者
Salehi, Peyman [2 ]
MaGee, David I. [1 ]
Dabiri, Minoo [3 ]
Torkian, Laleh [3 ]
Donahue, Jordan [1 ]
机构
[1] Univ New Brunswick, Dept Chem, Fredericton, NB E3B 5A3, Canada
[2] Shahid Beheshti Univ, Dept Phytochem, Med Plants & Drugs Res Inst, GC, Tehran 1983963113, Iran
[3] Shahid Beheshti Univ, Dept Chem, Fac Sci, GC, Tehran 1983963113, Iran
基金
加拿大自然科学与工程研究理事会;
关键词
Click chemistry; 1,2,3-Triazole; One-pot reaction; Multicomponent reaction; MCR; Phthalhydrazide; EFFICIENT ONE-POT; AZIDE CYCLOADDITION REACTIONS; SILICA SULFURIC-ACID; CHEMISTRY; 3-COMPONENT; PHTHALAZINE; DISCOVERY; CATALYST; WATER;
D O I
10.1007/s11030-011-9348-8
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
[(1,2,3-Triazol-4-yl)methoxy-phenyl]-2H-indazolo[2,1-b]phthalazine-trione derivatives were synthesized in a simple and efficient method from the one-pot four-component condensation reaction of phthalhydrazide, aromatic propargyloxy aldehydes, active methylene compounds (dimedone and 1,3-cyclohexanedione), and azides in the presence of Cu(OAc)(2)/sodium ascorbate and p-toluenesulfonic acid as catalysts in good to excellent yields.
引用
收藏
页码:231 / 240
页数:10
相关论文
共 35 条
  • [1] A versatile synthesis of fused triazolo derivatives by sequential Ugi/alkyne-azide cycloaddition reactions
    Akritopoulou-Zanze, I
    Gracias, V
    Djuric, SW
    [J]. TETRAHEDRON LETTERS, 2004, 45 (46) : 8439 - 8441
  • [2] 1,2,3-TRIAZOLE-[2',5'-BIS-O-(TERT-BUTYLDIMETHYLSILYL)-BETA-D-RIBOFURANOSYL]-3'-SPIRO-5''-(4''-AMINO-1'',2''-OXATHIOL 2'',2''-DIOXIDE) (TSAO) ANALOGS - SYNTHESIS AND ANTI-HIV-1 ACTIVITY
    ALVAREZ, R
    VELAZQUEZ, S
    SANFELIX, A
    AQUARO, S
    DECLERCQ, E
    PERNO, CF
    KARLSSON, A
    BALZARINI, J
    CAMARASA, MJ
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (24) : 4185 - 4194
  • [3] STUDIES ON 1,2,3-TRIAZOLES .13. (PIPERAZINYLALKOXY)[1]BENZOPYRANO[2,3-D]-1,2,3-TRIAZOL-9(1H)-ONES WITH COMBINED H-1 ANTIHISTAMINE AND MAST-CELL STABILIZING PROPERTIES
    BUCKLE, DR
    ROCKELL, CJM
    SMITH, H
    SPICER, BA
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (11) : 2262 - 2267
  • [4] A novel three-component, one-pot synthesis of 1,2-dihydro-1-arylnaphtho [1,2-e][1,3]oxazine-3-one derivatives under microwave-assisted and thermal solvent-free conditions
    Dabiri, Minoo
    Delbari, Akram Sadat
    Bazgir, Ayoob
    [J]. SYNLETT, 2007, (05) : 821 - 823
  • [5] Synthesis of Diheterocyclic Compounds Based on Triazolyl Methoxy Phenylquinazolines via a One-Pot Four-Component-Click Reaction
    Dabiri, Minoo
    Salehi, Peyman
    Bahramnejad, Mahboobeh
    Sherafat, Fatemeh
    [J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 2010, 12 (05): : 638 - 642
  • [6] Fung-Tomc JC, 1998, ANTIMICROB AGENTS CH, V42, P313
  • [7] Substituent effects on the antibacterial activity of nitrogen-carbon-linked (azolylphenyl)oxazolidinones with expanded activity against the fastidious gram-negative organisms Haemophilus influenzae and Moraxella catarrhalis
    Genin, MJ
    Allwine, DA
    Anderson, DJ
    Barbachyn, MR
    Emmert, DE
    Garmon, SA
    Graber, DR
    Grega, KC
    Hester, JB
    Hutchinson, DK
    Morris, J
    Reischer, RJ
    Ford, CW
    Zurenko, GE
    Hamel, JC
    Schaadt, RD
    Stapert, D
    Yagi, BH
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (05) : 953 - 970
  • [8] An efficient one-pot synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives
    Ghahremanzadeh, Ramin
    Shakibaei, Ghazaleh Imani
    Bazgir, Ayoob
    [J]. SYNLETT, 2008, (08) : 1129 - 1132
  • [9] γ-Methyl-substituted-γ-butyrolactones:: solid-phase synthesis employing a cyclisation-cleavage strategy
    Gouault, N
    Cupif, JF
    Sauleau, A
    David, M
    [J]. TETRAHEDRON LETTERS, 2000, 41 (38) : 7293 - 7297
  • [10] Synthesis of fused triazolo-imidazole derivatives by sequential van Leusen/alkyne-azide cycloaddition reactions
    Gracias, V
    Darczak, D
    Gasiecki, AF
    Djuric, SW
    [J]. TETRAHEDRON LETTERS, 2005, 46 (52) : 9053 - 9056