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

다국어 초록 (Multilingual Abstract)

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.

참고문헌 (Reference)

1 박명숙, "p-TSA를 이용한 퀴놀론 유도체의 비대칭 이합체 합성" 대한약학회 48 (48): 202-206, 2004

2 Ju-Hee Kim, "Synthesis of Novel 2,3-Dihydro-2-phenylquinolone Dimers Using β-Ketoester and N-Alkylaniline" 대한화학회 27 (27): 1249-1252, 2006

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