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The “Off‐Shore” Construction of Optionally Substituted 4‐Trifluoromethyl‐2‐quinolinones
Author(s) -
Leroux Frédéric,
Lefebvre Olivier,
Schlosser Manfred
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600140
Subject(s) - chemistry , trifluoromethyl , piperidine , aryl , organic chemistry , ylide , medicinal chemistry , alkyl
Treatment of ortho ‐lithiated tert ‐butyl N ‐arylcarbamates (i.e., BOC‐protected anilines) with N ‐(trifluoroacetyl)piperidine provides 2‐( N ‐BOC‐amino)aryl trifluoromethyl ketones which, upon consecutive reaction with an α‐alkoxycarbonyl‐substituted phosphorus ylide and acid (or base) yields 4‐trifluoromethyl‐2‐quinolinones which may bear additional substituents at any available position. The method is convenient and expedient. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)