• Title/Summary/Keyword: Bromination

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Selective Monobromination of 1,3-Diones with N-Bromosaccharin/Mg(ClO4)2 System in Solution and under Solvent-Free Conditions

  • Alinezhad, Heshmatollah;Tajbakhsh, Mahmood;Tehrani, Shahram Shahriari
    • Bulletin of the Korean Chemical Society
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    • v.32 no.5
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    • pp.1543-1546
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    • 2011
  • N-Bromosaccharin/$Mg(ClO_4)_2$ is an effective and regioselective system for ${\alpha}$-monobromination of 1,3-dicarbonyl compounds. A wide variety of ${\beta}$-keto esters and 1,3-diketones in reaction with this system afforded a regioselectively ${\alpha}$-monobrominated products. The bromination reaction can be conducted at 0-5 $^{\circ}C$ either in solution or under solvent-free conditions.

Synthesis of Potential COX-2 Inhibitory 1,5-Diarylhydantoin Derivatives (잠재적 COX-2 억제작용이 있는 1,5-Diarylhydantoin유도체의 합성)

  • 권순경;박해선
    • YAKHAK HOEJI
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    • v.48 no.2
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    • pp.135-140
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    • 2004
  • For the development of new COX-2 inhibitors, 1,5-diarylhydantoins 5a∼5c and 1,5-diaryl-2-thiohydantoin 6a∼6c were synthesized from commercially available phenylacetic acids through esterification, bromination, C-N bond formation and cyclization. Esters 2a∼c were efficiently synthesized from the starting materials 1a∼c by refluxing in absolute methanol for 3 hours with catalytic concentrated sulfuric acid. Bromination of 2a∼c was carried out with use of N-bomosuccinimide at rt in dichloromethane. The bromine of 3a∼c was substituted with aniline in ethanol or N,N-dimethylformamide to provide 4a∼c. Hydantoins and 2-thiohydantoins were synthesized from 4a∼c by treatment of potassium isocyanate or potassium thiocyanate in dil-ethanol with triethylamine.

Synthesis and Characterization of Novel Hydantoins as Potential COX-2 Inhibitors: 1,5-Diarylhydantoins

  • Park, Hae-Sun;Choi, Hee-Jeon;Shin, Hea-Soon;Lee, Sang-Kook;Park, Myung-Sook
    • Bulletin of the Korean Chemical Society
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    • v.28 no.5
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    • pp.751-757
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    • 2007
  • To develop new COX-2 inhibitors, 1,5-diarylhydantoins and 1,5-diaryl-2-thiohydantoins were synthesized from phenylacetic acids by esterification, bromination, C-N bond formation and cyclization. Esters 1-3 were efficiently synthesized from the starting materials by reflux in absolute methanol for 3 h containing concentrated sulfuric acid as catalyst. Bromination was carried out with N-bromosuccinimide at rt in dichloromethane. Bromides 4-6 were reacted with aniline, p-anisidine, sulfanilamide in ethanol (or N,N-dimethylformamide) to provide the amines 7-15. Hydantoins and 2-thiohydantoins 16-46 were synthesized from amines 7-15 by treating them with potassium isocyanate (or potassium thiocyanate) and triethylamine. The synthetic process from alkyl α-anilinophenylacetate 7-15 to 3-alkylhydantoins was carried out in a one-pot reaction using alkyl isocyanate (alkyl isothiocyanate).

Gas Permeation Properties of Brominated Polysulfone Membranes (브롬화된 Polysulfone막에 의한 기체 투과 특성에 관한 연구)

  • Rhim, Ji-Won;Lee, Bo-Sung;Kim, Tae-Young;Kim, Dae-Hoon;Lee, Byung-Sung;Yoon, Seok-Won;Im, Hyeon-Soo
    • Membrane Journal
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    • v.19 no.2
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    • pp.150-156
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    • 2009
  • To improve the permselective efficiency of polysulfone membranes, the bromination was performed and then the resulting membranes were investigated in terms of membrane structures and gas transport characteristics. The brominated Polysulfone membranes were characterized by FT-IR, 1H-NMR, TGA, contact angle measurements, and gas permeation measurements were accomplished with He, $N_2,\;CO_2\;and\;O_2$. In general, the permeation rates were reduced while the selectivities increased as the bromination progressed.

Studies on the Synthesis of Geminal Bisphosphono Amine Derivatives Using Pentacovalent Oxaphospholenes (5배위 결합된 옥사포스포린을 이용한 제미널 비스포스포노 아민 유도체의 합성에 관한 연구)

  • Lee, Mi Young;Jung, Kang Yeoun
    • Journal of the Korean Chemical Society
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    • v.43 no.3
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    • pp.294-301
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    • 1999
  • Geminal bisphosphonates have been well known to be effective inhibitors of various calciumrelated disorders such as Paget's disease, hypercalcemia of malignancy, and osteoporosis. To synthesize bisphosphonates, we have used the pentacovalent oxaphospholene prepared from methyl vinyl ketone and triethyl-phosphite. Υ-Ketobisphosphonates are obtained by bromination, applied Westheimer reaction, and hydrolysis of synthesized oxaphospholene. This compound was converted to the N-alkylated Υ-aminobisphosphonates by the reductive amination. Conversion of the resulting secondary amine to the tertiary one, followed by introduction of the second alkyl group on the nitrogen, was led to the synthesis of new N,N'-dialkylated Υ-aminobisphosphonates.

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