The "off-shore" construction of optionally substituted 4-trifluoromethyl-2-quinolinones
Leroux, Frederic; Lefebvre, Olivier; Schlosser, Manfred
2006

Abstract

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)]

Details

Title The "off-shore" construction of optionally substituted 4-trifluoromethyl-2-quinolinones
Author(s) Leroux, Frederic ; Lefebvre, Olivier ; Schlosser, Manfred
Published in European Journal of Organic Chemistry
Issue 14
Pages 3147-3151
Date 2006
ISSN 1434-193X
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
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)
DOI https://doi.org/10.1002/ejoc.200600140
Other identifier(s) View record in Web of Science
DAR: 8949
Laboratories LSCO
Record Appears in Scientific production and competences > SB - School of Basic Sciences > SB Archives > LSCO - Laboratory of Organic Synthesis and Catalysis
Peer-reviewed publications
Work produced at EPFL
Journal Articles
Published
Record creation date 2007-03-07

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