One-Pot Synthesis of Triazoloquinazolinones via Copper-Catalyzed Tandem Click and Intramolecular C-H Amidation

被引:38
作者
Selvaraju, Manikandan [1 ]
Sun, Chung-Ming [1 ]
机构
[1] Natl Chiao Tung Univ, Dept Appl Chem, Hsinchu 30010, Taiwan
关键词
CH amidation; copper-catalyzed reaction; one-pot protocol; tandem reactions; triazoloquinazolinones; DIRECT ARYLATIONS; DIRECT AMINATION; ORGANIC AZIDES; DIVERSITY; LIGATION;
D O I
10.1002/adsc.201301013
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A novel and highly efficient copper-catalyzed tandem synthesis of triazoloquinazolinones is explored. The synthetic strategy involves a sequential one-pot click reaction followed by aerobic intramolecular CH amidation. Two distinct and important transformations were carried out in one-pot by employing a single cost-effective copper catalyst. The milder, rapid and ligand-free reaction conditions as well as a broader substrate scope are the salient features of this novel protocol.
引用
收藏
页码:1329 / 1336
页数:8
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共 55 条
  • [1] Palladium-catalyzed direct arylations of 1,2,3-triazoles with aryl chlorides using conventional heating
    Ackermann, Lutz
    Vicente, Ruben
    Born, Robert
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (05) : 741 - 748
  • [2] Regioselective syntheses of fully-substituted 1,2,3-triazoles: the CuAAC/C-H bond functionalization nexus
    Ackermann, Lutz
    Potukuchi, Harish Kumar
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (20) : 4503 - 4513
  • [3] Palladium-Catalyzed Dehydrogenative Direct Arylations of 1,2,3-Triazoles
    Ackermann, Lutz
    Jeyachandran, Rajkumar
    Potukuchi, Harish K.
    Novak, Petr
    Buettner, Lea
    [J]. ORGANIC LETTERS, 2010, 12 (09) : 2056 - 2059
  • [4] Catalytic Direct Arylations in Polyethylene Glycol (PEG): Recyclable Palladium(0) Catalyst for C-H Bond Cleavages in the Presence of Air
    Ackermann, Lutz
    Vicente, Ruben
    [J]. ORGANIC LETTERS, 2009, 11 (21) : 4922 - 4925
  • [5] Synthesis and pharmacological investigation of novel 4-benzyl-1-substituted-4H-[1,2,4]triazolo[4,3-a]quinazolin-5-ones as new class of H1-antihistaminic agents
    Alagarsamy, V.
    Solomon, V. R.
    Murugan, M.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (12) : 4009 - 4015
  • [6] 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
  • [7] Substituted 1,2,3-triazolo[1,5-a]quinazolines: synthesis and binding to benzodiazepine and adenosine receptors
    Bertelli, L
    Biagi, G
    Giorgi, I
    Livi, O
    Manera, C
    Scartoni, V
    Lucacchini, A
    Giannaccini, G
    Barili, PL
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2000, 35 (03) : 333 - 341
  • [8] Organic azides:: An exploding diversity of a unique class of compounds
    Bräse, S
    Gil, C
    Knepper, K
    Zimmermann, V
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (33) : 5188 - 5240
  • [9] Brase S., 2005, ANGEW CHEM, V117, P5320, DOI DOI 10.1002/ANGE.200400657
  • [10] Rapid diversity-oriented synthesis in microtiter plates for in situ screening of HIV protease inhibitors
    Brik, A
    Muldoon, J
    Lin, YC
    Elder, JH
    Goodsell, DS
    Olson, AJ
    Fokin, VV
    Sharpless, KB
    Wong, CH
    [J]. CHEMBIOCHEM, 2003, 4 (11) : 1246 - 1248