• 제목/요약/키워드: N-Arylation

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

  • 이준영;양민호;백승욱
    • 공업화학
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    • 제19권6호
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    • pp.629-632
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    • 2008
  • N-Arylation에 대한 경제적이고 실용적인 촉매시스템을 찾기 위하여 indole을 이용한 다양한 반응조건에서 실험이 수행되었으며, 결과적으로 본 연구에서 처음 시도한 copper nitrate와 copper cabonate가 다른 copper계 촉매나 palladium 촉매에 유사하거나 더 우수한 반응성을 보여주었다. Copper nitrate 촉매를 사용하는 경우에는 다양한 리간드 중에서 N,N'-dimethylethylenediamine 리간드가 더 효과적이었으며 copper cabonate 계에서는 ethylenediamine 리간드가 더 적합한 것으로 판명되었다.

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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    • 제31권8호
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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.

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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    • 제32권12호
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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.

Donor-Acceptor 발색단과 디케토피롤로피롤(DPP) 유도체에 관한 연구 (The Study of Donor-Acceptor Chromophores and Diketopyrrolopyrrole(DPP) Analogues)

  • 김헌수;김승회;박수열
    • Tribology and Lubricants
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    • 제32권5호
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    • pp.141-146
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    • 2016
  • The diketopyrrolopyrrole (DPP) pigment is a bicyclic 8-π-electron system containing two lactam units. Typical DPP derivative pigments have melting points of over 350°C and very low solubility in most solvents, and show absorption in the visible region with a molar extinction coefficient of 33,000 dm2mol−1 and strong photoluminescence with maxima in the range 500–600 nm. X-ray structure analyses of DPP show that the whole molecule is almost in one plane. The phenyl rings are twisted out of the heterocyclic plane and the intermolecular hydrogen bonding between neighboring lactam NH and carbonyl units influences the structure of the DPP pigment in the solid state. In this study, mono-N-alkylation and mono-N-arylation were undertaken for Pigment Red 264 or Pigment Orange 73 with alkyl halide and aryl halide, respectively, in the presence of sodium tert-butoxide as a base catalyst to improve the solubility of DPP pigments and their application as CO2 indicators. The synthetic yield was in the range 11–88%. The indicator dyes are highly soluble in organic solvents and shows pH-dependent absorption (λmax 501 and 572 nm for the protonated and deprotonated forms, respectively) and emission (λmax 524 and 605 nm for the protonated and deprotonated forms, respectively) spectra. The mono-N-alkylated and mono-N-arylated DPP pigment was identified by 1H-NMR (1H-Nuclear Magnetic Resonance Spectrometer), FT-IR (Fourier Transform Infrared Spectroscopy), and MS (Mass Spectrometry). According to the results of color and hue properties obtained by a color matching analyzer, the synthesized DPP pigment material can be used as a CO2 indicator.

Synthesis of Oxazolidinone Phosphonate Derivatives, Part I

  • Hwang, Jae-Min;Shin, Woon-Seob;Jung, Kang-Yeoun
    • Bulletin of the Korean Chemical Society
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    • 제25권9호
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    • pp.1326-1330
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    • 2004
  • Several new derivatives of oxazolidinone phosphonate, that are expected to show biological activity, were prepared efficiently by previously published methods. ${\gamma}$-Ketophosphonate 1 was synthesized using pentacovalent oxaphosphorane chemistry followed by reductive amination with aromatic amine of oxazolidinone 4. Biological activity of the synthetic compounds has been studied. One of the synthetic compounds showed promising result for us to pursue further studies.

Synthesis of N,N-Diaryl-(pyridin-3-yl)pyrimidin-2-amine Derivatives and Their Photochemical Properties

  • El-Deeb, Ibrahim Mustafa;Lee, So-Ha
    • 한국응용과학기술학회지
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    • 제25권3호
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    • pp.291-298
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    • 2008
  • Although the pyrimidine derivatives were obtained in low yields ranging from 8% to 20%, we reported the successful preparation of N,N-diaryl-pyrimidin-2-amine derivatives starting from the corresponding 2-aminopyrimidines (1a-1c), by direct palladium-catalyzed arylation using different arylbromides. The reasons of low yields are thought to be the electronic and steric effects by the neighboring aromatic systems. The absorption spectra and photoluminescent spectra of compounds (3a 3g and 4a-4c) were measured using dichloromethane on the concentration of 25 mM by UV vis spectroscopy and luminescent spectroscopy. Pyrimidine derivatives 4a, 4b, and 4c showed moderate emission maxima at 474 nm, 481 nm, and 367 nm, respectively, while other compounds showed very weak photoluminescence or no photoluminescence at all.

Synthesis and $^1$H-nmr of N-Arylated Nitrogen-Containing Aromatic Heterocycles

  • Koh Park, Kwang-Hee;Lee, Jae-Bong;Han, Du-Hee
    • Bulletin of the Korean Chemical Society
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    • 제6권3호
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    • pp.141-144
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    • 1985
  • N-Arylation reaction of nitrogen-containing heterocycles such as pyridine, nicotinamide and 4,4'-bipyridine was studied. We prepared N-2,4-dinitrophenyl derivatives initially by reacting the above heterocycles with 2,4-dinitrochlorobenzene in ethanol, and then treated the N-2,4-dinitrophenylated heterocycles with various aniline derivatives, $XC_6H_4NH_2$(X = -H, p-$CH_3$, p-$C_2H_5$, p-Cl, p-CN, p-OH, p-$OCH_3$, o-Cl, m-$CH_3$) to yield the corresponding N-arylated compounds in fairly good yields. $H^1$-nmr patterns and peak assignments of the N-arylated products were described.

Arylation of Styrene by Palladium Acetate-Phosphine Complexes

  • 황박영애;황성원
    • Bulletin of the Korean Chemical Society
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    • 제18권2호
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    • pp.218-221
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    • 1997
  • When phenylation of styrene was carried out in the presence of Pd(OAc)2 and PPh3 in benzene, trans-stilbene was obtained in good yield (566%) with high selectivity (98%) under mild condition (55 ℃, 50 psi O2, 20 h). Since trans-stilbene could be produced not only from benzene but also from phenyl group of PPh3 by migration of its phenyl group to Pd, the competitiveness of benzene and the migratory aptitude of aryl group of triarylphosphine toward styrene has been investigated with various phosphines (PR3: P(p-C6H4CH3)3, P(p-C6H4OCH3)3, P(p-C6H4F)3, P(p-C6H4Cl)3, P(C6H5)3, P(C6H11)3, P(OC4H9n)3, P(CH2C6H5)3 and P(C6F5)3). The yield and selectivity toward trans-stilbene are increased as the basicity of the phosphines increases. The composition of arylated olefin from arylphosphine, in turn, increases as the electronegativity of the substituent on the aryl group of arylphosphines increases.