3-haloquinolines by friedlander reaction of α-haloketones

SV Ryabukhin, VS Naumchik, AS Plaskon…

Index: Ryabukhin, Sergey V.; Naumchik, Vasiliy S.; Plaskon, Andrey S.; Grygorenko, Oleksandr O.; Tolmachev, Andrey A. Journal of Organic Chemistry, 2011 , vol. 76, # 14 p. 5774 - 5781

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Citation Number: 30

Abstract

A general approach to 3-fluoro-, 3-chloro-, and 3-bromoquinolines which relies on organosilane-promoted Friedländer reaction of α-haloketones is described. The scope of the methylene component as well as influence of the organosilane component on the outcome of the reaction is studied. The method can be used under parallel synthesis conditions.

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551-93-9

2'-Aminoacetophenone

Chloroacetone Structure

78-95-5

Chloroacetone

~47%

3-chloro-2,4-dimethylquinoline Structure

59280-68-1

3-chloro-2,4-di...

2'-Aminoacetophenone Structure

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2'-Aminoacetophenone

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1,3-Dichloroacetone

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3-Chloro-2-(chloromethyl)-4-methylquinoline hydrochloride Structure

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3-Chloro-2-(chl...

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53896-48-3

1-(4-chlorophen...

2-Aminobenzophenone Structure

2835-77-0

2-Aminobenzophenone

~94%

2-(4-chlorophenyl)-4-phenylquinoline Structure

1236-90-4

2-(4-chlorophen...

2,4'-dichloroacetophenone Structure

937-20-2

2,4'-dichloroac...

2-Aminobenzophenone Structure

2835-77-0

2-Aminobenzophenone

~91%

2-(4-chlorophenyl)-4-phenylquinoline Structure

1236-90-4

2-(4-chlorophen...

2-Bromo-4'-chloroacetophenone Structure

536-38-9

2-Bromo-4'-chlo...

2-Aminobenzophenone Structure

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2-Aminobenzophenone

~71%

2-(4-chlorophenyl)-4-phenylquinoline Structure

1236-90-4

2-(4-chlorophen...


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