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Synthesis 2009(18): 3113-3119  
DOI: 10.1055/s-0029-1216933
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

New Functional Derivatives of 9-Phenylquinine

Przemysaw J. Boratyński, Jacek Skarżewski*
Department of Organic Chemistry, Faculty of Chemistry, Wrocaw University of Technology, Wyspiańskiego 27, Wrocaw 50-317, Poland
Fax: +48(71)3284064; e-Mail: jacek.skarzewski@pwr.wroc.pl;
Further Information

Publication History

Received 14 March 2009
Publication Date:
14 August 2009 (online)

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Abstract

A rapid synthesis of various 9-aryl derivatives of quinine is presented. They are obtained via coupling reactions of functionalized arylmagnesium halides and 9-chloroquinine.

Key words

cinchona alkaloid - Grignard reaction - chiral pool - coupling reaction - quinine

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(9S)-9-Chloroquinine (1) is not very soluble in toluene at r.t.; more concentrated solutions can be obtained by dissolving 1 in toluene at 100 ˚C then cooling.