• Title/Summary/Keyword: arylation

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A Study on N-Arylation of Indole Using Copper Nitrate or Copper Carbonate as a Catalyst (Copper Nitrate와 Copper Carbonate를 촉매로 이용한 Indole의 N-Arylation 연구)

  • Lee, Jun Young;Yang, Min Ho;Paik, Seung Uk
    • Applied Chemistry for Engineering
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    • v.19 no.6
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    • pp.629-632
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    • 2008
  • N-Arylation of indole with aryl iodides has been achieved by employing copper nitrate or copper cabonate as a catalyst, which might be more practical and economical over any other copper- or palladium-based catalysts for industrial applications. N,N'-dimethylethylenediamine was found to be the most effective with copper nitrate catalyst systems, while ethylenediamine was the most active with copper carbonate.

C-H Arylation of Nitroimidazoles and Nitropyrazoles Guided by the Electronic Effect of the Nitro Group

  • Jung, Haeun;Bae, Seri;Jang, Ha-Lim;Joo, Jung Min
    • Bulletin of the Korean Chemical Society
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    • v.35 no.10
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    • pp.3009-3014
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    • 2014
  • A palladium-catalyzed C-H arylation reaction of nitroimidazoles and nitropyrazoles was developed using aryl bromides as arene donors. The electron-withdrawing effect of the nitro group allows for direct C-H arylation reactions of the nitro diazoles with high regioselectivity under mild conditions. The new C-H arylation approach is thus complementary to nucleophilic substitution reactions, enabling the preparation of complex nitroazole compounds.

Facile Access to a Variety of 2,5-Biaryl-1,2,4-triazol-3-ones via Regioselective N-Arylation of Triazolones

  • Park, Ji-Yeon;Chae, Jung-Hyun
    • Bulletin of the Korean Chemical Society
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    • v.31 no.8
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    • pp.2143-2146
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    • 2010
  • A selective synthetic method of the 2,5-biaryltriazolones has been developed via copper-catalyzed N-arylation reaction. Aryltriazolones, which were readily prepared from commercially available compounds, were N-arylated to 2,5-biaryltriazolones with high regioselectivity. This approach allows for access to a variety of 2,5-biaryl-1,2,4-trizol-3-ones in a simple and practical manner.

Pd-Catalyzed Oxidative Arylation of Cinnamylphosphonates: An Efficient Synthesis of (Z)-Alkenylphosphonates

  • Lee, Hyun Seung;Lim, Cheol Hee;Lee, Hyun Ju;Kim, Jae Nyoung
    • Bulletin of the Korean Chemical Society
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    • v.33 no.11
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    • pp.3817-3822
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    • 2012
  • Various alkenylphosphonates were prepared via the palladium-catalyzed oxidative arylation of cinnamylphosphonates with arenes. The regioselectivity during the ${\beta}$-H elimination of the corresponding alkylpalladium intermediate was governed most likely by steric factors.

Diversification of 4,5-disubstituted Pyrrolo[3,2-d]-pyrimidines by Microwave Assisted Metal Catalyzed Reaction (마이크로파와 금속 촉매를 이용한 Pyrrolo[3,2-d]-pyrimidine 유도체의 다양화)

  • Jeong Seob, Byeon;Eul Kgun, Yum;Yeong-Joon, Kim
    • Journal of the Korean Chemical Society
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    • v.66 no.6
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    • pp.442-450
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    • 2022
  • Diverse pyrrolo[3,2-d]pyrimidines that are expected to exhibit bioactivity were synthesized through O-arylation and Suzuki coupling reactions. Microwave-assisted O-arylation was successfully performed using a Cu metal catalyst, so that 4 position of pyrrolo[3,2-d]pyrimidine could be substituted with phenol group. In addition, 4-aryl substituted pyrrolo[3,2-d]pyrimidines were synthesized with good to excellent yields by microwave-assisted Suzuki coupling reaction using a Pd metal catalyst. By using microwaves as reaction conditions for diversification of derivatives, it was possible to dramatically overcome the disadvantages of traditional heat reactions of long reaction times and heat transfer efficiency problems. The result of this study can be used to be diversify pyrrolo[3,2-d]pyrimidine derivatives, which are expected to play an important role in the drug discovery research.

Rhodium-Catalyzed Highly Regioselective C-H Arylation of Imidazo[1,2-a]pyridines with Aryl Halides and Triflates

  • Liu, Yi;He, Lin;Yin, Guoqiang;Wu, Guojie;Cui, Yingde
    • Bulletin of the Korean Chemical Society
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    • v.34 no.8
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    • pp.2340-2342
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    • 2013
  • A convenient Rh-catalyzed C-H arylation of imidazo[1,2-a]pyridines with a variety of aryl halides or triflates has been reported. This process afforded a range of biaryl compounds in excellent yields and showed high activity and broad scope.

Effects of Various Quinones (Menadione, Benzoquinone and 2,3-Dimethoxy-1,4-naphthoquinone) on Rat Platelets (Quinones (menadione, benzoquinone, 및 2,3-dimethoxy-1,4-naphthoquinone)의 혈소판 세포독성)

  • 승상애;이무열;이주영;김미정;정진호
    • Toxicological Research
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    • v.12 no.2
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    • pp.289-293
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    • 1996
  • Our previous studies demonstrated that quinone (menadione) is cytotoxic to rat platelets. In an attempt to assess the relative contributions of redox cycling and/or arylation in quinone-induced cytotoxicity, we have studied three quinones with different mechanisms: 2, 3-dimethoxy-1, 4-naphthoquinone (DMNQ; pure redox cycler), menadione (both redox cycler and arylator), and 1, 4-benzoquinone (pure arylator). The order of redox cycling capacity in platelet rich plasma (PRP) isolated from rats was menadione>DMNQ>1, 4-benzoquonone, which was consistent with the previous studies using isolated hepatocytes. 1, 4-Benzoquinone was more toxic to rat platelets than menadione, while DMNQ did not cause cell death at all. Lactate dehydrogenase inhibition studies revealed that 1, 4-benzoquinone inhibited significantly in a time-dependent manner, while menadione and DMNQ did not at all. These results suggested that arylation by quinone compounds might play a critical role in quinone-induced cytotoxicity in rat platelets.

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Microwave Assisted, Solvent- and Ligand-Free Copper Catalyzed N-Arylation of Phenylurea with Aryl Halides

  • Gavade, Sandip;Shingare, Murlidhar;Mane, Dhananjay
    • Bulletin of the Korean Chemical Society
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    • v.32 no.12
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    • pp.4167-4170
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    • 2011
  • An inexpensive and efficient catalyst system has been developed for the N-arylation of phenylurea including a variety of aryl halides. This simple protocol uses $Cu_2O$ as the catalyst, microwave assisted, solvent- and ligand-free, $K_3PO_4{\cdot}H_2O$ as the base.