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2-Phenyl-4-quinolones와 Methyl Iodide의 친핵반응에 의한 유도체의 합성
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  • 2-Phenyl-4-quinolones와 Methyl Iodide의 친핵반응에 의한 유도체의 합성
  • Nucleophilic Reaction of 2-Phenyl-4-quinolones with Methyl Iodide and Preparation of Its Derivatives
저자명
오미정,박명숙,Oh. Mi-Jung,Park. Myung-Sook
간행물명
약학회지
권/호정보
2008년|52권 6호|pp.514-519 (6 pages)
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이 논문은 한국과학기술정보연구원과 논문 연계를 통해 무료로 제공되는 원문입니다.
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기타언어초록

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 ${eta}$-ketoesters 2a-h, which can be readily obtained from the corresponding anilines 1a-e by reaction with ethyl bezoylacetates.