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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 35, Number 5
JKCSEZ 35(5)
October 20, 1991 

A Study of the Competitive Reaction of C-Acylation Versus O-Acylation on the 3,4-Dichloroacetophenone

3,4-디클로로아세토페논에 대한 C-아실화와 O-아실화의 경쟁적 반응에 관한 연구
You Seung Kim, He Duck Mah, Hyoung Sug Kim

김유승, 마혜덕, 김형석
본 연구는 퀴놀론 중간체 합성을 위한 모델 연구로서 3,4-디클로로아세토페논의 C-, O-아실화의 경쟁반응에 대해 조사하였다. 3,4-디클로로아세토페논의 C-, O-아실화 비율에 대한 염기, 용매, 아실화물의 이탈기 효과에 대해 논하였으며, 이 때 아실화물로는 클로로포름산에틸, 에틸페닐탄산, 그리고 디에틸탄산을 사용하였다. 비극성 용매에서, 사용된 염기의 금속이온 크기가 작으면 작을수록 C-아실화 반응이 지배적으로 일어났다. 이탈기 영향에 있어서는 아실화물의 이탈기 능력이 감소할수록 C-아실화 생성물이 증가함을 볼 수 있었다. 또한 용매의 극성이 감소할수록 C/O-아실화 비율이 증가함을 관찰하였다.

Quinolone derivatives have been used as antibacterial agents. In this work, the competitive C-and O-acylation reaction of 3,4-dichloroacetophenone, as a model study for the synthesis of quinolone intermediate, is studied. The effects of various bases, solvents and the leaving groups of acylating agents on the ratio of C-versus O-acylation of 3,4-dichloroacetophenone are elucidated by means of employing ethylchloroformate, ethylphenylcarbonate and diethylcarbonate as acylating agents. In aprotic solvents, C-acylation reactions occur more predominantly as the size of metal ions composing bases becomes smaller. Regarding the effects of leaving groups, it is shown that C-acylation product is increased as the ability of leaving groups of acylating agents decreases. The ratio of C/O-acylation is also observed to be increased as the polarity of solvents decreases.

580 - 585
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