• Title/Summary/Keyword: Dean-Stark apparatus

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Nucleophilic Reaction of 2-Phenyl-4-quinolones with Methyl Iodide and Preparation of Its Derivatives (2-Phenyl-4-quinolones와 Methyl Iodide의 친핵반응에 의한 유도체의 합성)

  • Oh, Mi-Jung;Park, Myung-Sook
    • YAKHAK HOEJI
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    • v.52 no.6
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    • pp.514-519
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    • 2008
  • We developed a convenient synthetic route to 3-alkylated 2-phenyl-4-quinolone derivatives (4a-h and 5a-c), which were expected to retain antitumor activity. A series of 2,3-dihydro-2-hydroxy-2-phenyl-4-quinolones (3a-h) was synthesized through dehydration, dealcoholation and hydration using acid-catalyzed one-pot reaction from anilines and ethyl benzoylacetates. 3-Methyl (or 3,3-dimethyl)-2-phenyl-4-quinolone derivatives 4 and 5 were synthesized from 3a-h through the methylation using methyl iodide. Formation of quinolone nucleus was undertaken with p-toluenesulfonic acid (p-TSA) at $90{\sim}110^{\circ}C$ in toluene for 3${\sim}$7.5 hr over the Dean-Stark apparatus. The key intermediates in these preparations are ${\beta}$-ketoesters 2a-h, which can be readily obtained from the corresponding anilines 1a-e by reaction with ethyl bezoylacetates.

Synthesis of Asymmetric Dimer of Quinolone Derivatives Using p-TSA (p-TSA를 이용한 퀴놀론 유도체의 비대칭 이합체 합성)

  • 박명숙
    • YAKHAK HOEJI
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    • v.48 no.3
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    • pp.202-206
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    • 2004
  • New asymmetric dimers, N,N'-dialkyl-4'-hydroxy-4-oxo-2,2',3,3'-tetrahydro-2,2'-diphenyl-4,4'-quinolones 3a-f were synthesized through the dehydration and dea1coholation of N-alkylanilines and ethyl benzoylacetate. Dimers 3a-f were identified by NMR, IR and GC-MS. A series of dimer 3a-f has been synthesized using acid-catalyzed one-pot reaction that involved the condensation, cyc1ization and dimerization. Similarly, the 6,6'-methoxy (or 7,7'-methoxy) substituted dimers were prepared from N-alkyl-meta-(or para)-anisidines. Formation of dimers was undertaken with p-toluenesulfonic acid (p-TSA) at 90∼11$0^{\circ}C$ in toluene for 2∼6 hours over the Dean-Stark apparatus.

Composition of Free Amino Acids and Essential Oils in Root of Anthriscus sylvestylis (전조 뿌리의 유리 아미노산과 정유 성분 조성)

  • 김상국;권태용;민기군;이승필;최부술;이상철
    • KOREAN JOURNAL OF CROP SCIENCE
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    • v.41 no.5
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    • pp.521-525
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    • 1996
  • The study was carried out to find compositions of proximate components, free amino acid, and essential oils from root of Anthriscus sylvestylis. Proximate component contents were 7.69% for protein, 1.74% for fat, 2.44% for fiber, and 3.76% for ash. Extract content was 27.68% in fresh root. The compositions of free amino acids consisted 16 kinds. Phenylalanine content was the highest in composition of free amino acids. The essential oils of the root of Anthriscus sylvestylis was examined. $\alpha$-pinene, campreol, ,$\beta$-pinene, sabinene, myrcene, phellandrene, $\alpha$-terpinolene, d-limone, ${\gamma}$-terpinene, p-cymene, $\alpha$-terpinolene, carboxaldehyde, 3-cyc1ohexen-l-carboxaldehyde, 2-nonenal, isobornyl acetate, 4-terpineol, $\beta$-bisabolene, cis-piperitol, p-cymen-8-ol, BHT, methyl eugenol and 2-methoxy-4-vinyl-phenol were identified from the diethylether layers. Recovery yield of essential oils of Anthriscus sylvestylis of root was 0.58%. As a result, it was considered that the plant is worthy of cultivating as spice and medicinal crops.

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