The "off-shore" construction of optionally substituted 4-trifluoromethyl-2-quinolinones

Treatment of ortho-lithiated tert-Bu N-arylcarbamates (i.e., BOC-protected anilines) with N-(trifluoroacetyl)piperidine provides 2-(N-BOC-amino)aryl trifluoromethyl ketones which, upon reaction with an alpha-alkoxycarbonyl-substituted phosphorus ylide and acid (or base) yields 4-trifluoromethyl-2-quinolinones which may bear addnl. substituents at any available position. The method is convenient and expedient. [on SciFinder (R)]


Published in:
European Journal of Organic Chemistry, 14, 3147-3151
Year:
2006
Keywords:
Note:
CAN 145:356615
27-17
Heterocyclic Compounds (One Hetero Atom)
Laboratoire de Stereochimie (UMR CNRS 7509),Universite Louis Pasteur (ECPM),Strasbourg,Fr.
Journal
1434-193X
written in English.
340-07-8 (N-(Trifluoroacetyl)piperidine); 1099-45-2 (Ethyl triphenylphosphoranylideneacetate); 3422-01-3 (tert.-Butyl N-phenylcarbamate); 5717-37-3 (Ethyl methyltriphenylphosphoranylideneacetate); 60144-52-7; 141940-37-6; 201928-56-5 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of optionally substituted 4-trifluoromethyl-2-quinolinones from trifluoroacetylphenyl carbamates and phosphorus ylides); 328956-59-8P; 910299-57-9P; 910299-58-0P; 910299-59-1P; 910299-60-4P; 910299-61-5P; 910299-64-8P; 910299-65-9P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of optionally substituted 4-trifluoromethyl-2-quinolinones from trifluoroacetylphenyl carbamates and phosphorus ylides); 25199-84-2P (4-Trifluoromethyl-2(1H)-quinolinone); 910299-62-6P (4,6-Bis(trifluoromethyl)-2(1H)-quinolinone); 910299-63-7P (5-Methoxy-4-trifluoromethyl-2(1H)-quinolinone); 910299-66-0P (3-Methyl-4-trifluoromethyl-2(1H)-quinolinone); 910299-67-1P (3-Methoxy-4-trifluoromethyl-2(1H)-quinolinone) Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of optionally substituted 4-trifluoromethyl-2-quinolinones from trifluoroacetylphenyl carbamates and phosphorus ylides)
Other identifiers:
Laboratories:




 Record created 2007-03-07, last modified 2018-01-27


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