Synthesis, microwave-promoted catalytic activity in Suzuki-Miyaura cross-coupling reactions and antimicrobial properties of novel benzimidazole salts bearing trimethylsilyl group

被引:38
|
作者
Yilmaz, Ulku [1 ]
Kucukbay, Hasan [1 ]
Sireci, Nihat [2 ]
Akkurt, Mehmet [3 ]
Gunal, Selami [4 ]
Durmaz, Riza [4 ]
Tahir, M. Nawaz [5 ]
机构
[1] Inonu Univ, Fac Sci & Arts, Dept Chem, TR-44280 Malatya, Turkey
[2] Adiyaman Univ, Fac Educ, TR-02040 Adiyaman, Turkey
[3] Erciyes Univ, Fac Sci, Dept Phys, TR-38039 Kayseri, Turkey
[4] Inonu Univ, Fac Med, Dept Microbiol, TR-44280 Malatya, Turkey
[5] Univ Sargodha, Dept Phys, Sargodha, Pakistan
关键词
benzimidazole salt; carbene; palladium catalysis; coupling reaction; Suzuki-Miyaura coupling; microwave; antimicrobial activity; CARBENE COMPLEXES; SUBSTITUTED BENZIMIDAZOLE; ARYL CHLORIDES; PALLADIUM; HECK; ANTIBACTERIAL; PRECATALYSTS; DERIVATIVES; SYSTEM; WATER;
D O I
10.1002/aoc.1772
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A mixture of benzimidazole salts (2-7), Pd(OAc)(2) and K2CO3 in DMF-H2O catalyzes the Suzuki-Miyaura cross-coupling reactions promoted by microwave irradiation resulting in high yield within a short time. In particular, the yield of the Suzuki-Miyaura reactions with aryl bromides was found to be nearly quantitative. The synthesized benzimidazole salts (2-7) were identified by H-1-C-13, NMR, IR spectroscopic methods and microanalysis. The molecular structure of 1 was determined by X-ray crystallography. The antibacterial and antifungal activities of the novel benzimidazole derivatives (1-7) were also tested against standard strains. Copyright (C) 2011 John Wiley & Sons, Ltd.
引用
收藏
页码:366 / 373
页数:8
相关论文
共 50 条
  • [1] Synthesis, characterization, and microwave-promoted catalytic activity of novel benzimidazole salts bearing silicon-containing substituents in Heck-Mizoroki and Suzuki-Miyaura cross-coupling reactions under aerobic conditions
    Kucukbay, Hasan
    Sireci, Nihat
    Yilmaz, Ulku
    Deniz, Selma
    Akkurt, Mehmet
    Baktir, Zeliha
    Buyukgungor, Orhan
    TURKISH JOURNAL OF CHEMISTRY, 2012, 36 (02) : 201 - 217
  • [2] Microwave-Promoted Suzuki-Miyaura Cross-Coupling of Aryl Imidazolylsulfonates in Water
    Civicos, Jose F.
    Alonso, Diego A.
    Najera, Carmen
    ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (14-15) : 2771 - 2776
  • [3] Synthesis, Characterization and Microwave-Promoted Catalytic Activity of Novel N-phenylbenzimidazolium Salts in Heck-Mizoroki and Suzuki-Miyaura Cross-Coupling Reactions under Mild Conditions
    Yilmaz, Ulku
    Kucukbay, Hasan
    Deniz, Selma
    Sireci, Nihat
    MOLECULES, 2013, 18 (03) : 2501 - 2517
  • [4] Synthesis of biphenylamines via Suzuki-Miyaura cross-coupling reactions
    Maj, Anna M.
    Delaude, Lionel
    Demonceau, Albert
    Noels, Alfred F.
    TETRAHEDRON, 2007, 63 (12) : 2657 - 2663
  • [5] Synthesis and microwave-assisted catalytic activity of novel bis-benzimidazole salts bearing furfuryl and thenyl moieties in Heck and Suzuki cross-coupling reactions
    Yilmaz, Uelkue
    Sireci, Nihat
    Deniz, Selma
    Kucukbay, Hasan
    APPLIED ORGANOMETALLIC CHEMISTRY, 2010, 24 (05) : 414 - 420
  • [6] Microwave-promoted Suzuki-Miyaura coupling reactions in a cycloalkane-based thermomorphic biphasic system
    Hayashi, K
    Kim, S
    Kono, Y
    Tamura, M
    Chiba, K
    TETRAHEDRON LETTERS, 2006, 47 (02) : 171 - 174
  • [7] Suzuki-Miyaura cross-coupling reactions of aryl tellurides with potassium aryltrifluoroborate salts
    Cella, R
    Cunha, RLOR
    Reis, AES
    Pimenta, DC
    Klitzke, CF
    Stefani, HA
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (01): : 244 - 250
  • [8] Azidosubstituted arylboronic acids: synthesis and Suzuki-Miyaura cross-coupling reactions
    Sviridov, SI
    Vasi'ev, AA
    Sergovskaya, NL
    Chirskaya, MV
    Shorshnev, SV
    TETRAHEDRON, 2006, 62 (11) : 2639 - 2647
  • [9] Chemoselective Synthesis of Arylpyridines through Suzuki-Miyaura Cross-Coupling Reactions
    Perdomo Rivera, Rodisnel
    Ehlers, Peter
    Ohlendorf, Lars
    Torres Rodriguez, Eugenio
    Villinger, Alexander
    Langer, Peter
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (08) : 990 - 1003
  • [10] Synthesis of potassium heteroarylmethyltrifluoroborates and their use in Suzuki-Miyaura cross-coupling reactions
    Ryu, DaWeon
    Devulapally, Rammohan
    Molander, Gary A.
    Seapy, Dave G.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244