• Archives of Pharmacal Research
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• 제26권12호
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• pp.985-989
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• 2003

An efficient synthesis of 5-chloro-3-[4-(3-diethylaminopropoxy)benzoyl]-2-(4-methoxyphenyl)benzofuran (8), a potent $\beta$-amyloid aggregation inhibitor, is described. 5-Chloro-2-(4-methoxyphenyl)benzofuran (3) was obtained by the one-pot synthesis of 4-chlorophenol with $\omega$(methylsulfinyl)-p-methoxyacetophenone (1) under Pummerer reaction conditions, and it was followed by the desulfurization of the resultant 5-chloro-3-methylthio-2-(4-methoxyphenyl)benzofuran (2e). Acylation of benzofuran 3 with 4-(3-bromopropoxy)benzoyl chloride (6) gave the ketone 7, which was converted into compound 8 by the treatment of diethylamine.

• Bulletin of the Korean Chemical Society
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• 제35권6호
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• pp.1894-1896
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• 2014

• 농약과학회지
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• 제5권2호
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• pp.13-17
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• 2001

새로운 살균제를 개발할 목적으로 새로운 2-phenylimino-1,3-thiazoline 유도체를 합성하였다. Ketone dimer를 염소와 반응시킨 다음 중간체 8a의 분리없이 benzylamine으로 처리하여 ${\gamma}-Chloro-{\beta}-keto$ benzylamide 10a를 얻었다. Methyl isothiocyanate와 aniline 유도체의 반응에서 얻은 thiourea 4를 10a와 acetone 용액 중에서 반응시켜 분리 불가능한 중간체 11 및 12를 거쳐 각각에 상응하는 2-phenylimino-1,3-thiazoline 유도체의 염산염 2를 얻었다. Thiourea 4의 phenyl기에 인접한 질소원자의 비공유 전자쌍의 도움으로 황원자의 친핵적 공격을 포함한 가능한 반응 mechanism을 논의하였다.

• Bulletin of the Korean Chemical Society
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• 제17권1호
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• pp.50-55
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• 1996

Reaction of carbonyl compounds with diisopinocampheylhaloboranes (Ipc2BX,X=Cl, Br, I) was investigated in detail in order to establish their usefulness as selective reducing agents. The reagents reduced aldehydes and ketones to the corresponding alcohols. The reactivities are in the order of Ipc2BCl Ipc2BBr>Ipc2BI.The reagents also reduced ${\alpha}{\beta}-unsaturated$, aldehydes and ketones to the corresponding allylic alcohols without any detectable 1,4-reduction. Especially, the chloro derivative nicely achieved the selective reduction of aldehyde or ketone groups in the presence of many other functional groups. The most remarkable result of this investigation is that aldehydes and ketones can be selectively reduced in the presence of acid chlorides.