• Title/Summary/Keyword: 2,3-Dihydro-2-phenyl-4-quinolones

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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.