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Synthesis 1995; 1995(9): 1159-1162
DOI: 10.1055/s-1995-4053
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Synthesis of Substituted 8-Methoxyquinolines by Regioselective Bromine-Lithium Exchange of 5,7-Dihalo-8-methoxyquinolines and 7-Bromo-8-methoxyquinoline

François Trécourt, Marc Mallet, Florence Mongin, Guy Quéguiner*
  • *Laboratoire de Chimie Organique Fine Hétérocyclique de l’IRCOF associé au CNRS, INSA de Rouen, BP 08, F-76131 Mont-Saint-Aignan cédex, France, Fax +33(35)528484
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Publication Date:
31 December 2000 (online)

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Reaction of phenyllithium with 7-bromo-8-methoxyquinoline, 5,7-dibromo-8-methoxyquinoline and 5,7-diiodo-8-metehoxyquinoline has been studied. Thus, bromine-lithium exchange of 7-bromo-8-methoxyquinoline gave the 7-lithio-8-methoxyquinoline which reacted with various electrophiles to afford 7-substituted-8-methoxyquinolines 3a-e. The same procedure was also applied to 5,7-dibromo-8-methoxyquinoline, which because of the high regioselectivity of the reaction, led to 7-substituted 5-bromo-8-methoxyquinolines 4a-f; one of them was used for the preparation of a pyridopyranoquinoline.

bromine-lithium exchange - regioselectivity - phenyllithium - bromoquinoline - pyridopyranoquinoline