4-(trifluoromethyl)quinoline derivatives

Under carefully controlled conditions, Et 4,4,4-trifluoroacetoacetate (Et 4,4,4-trifluoro-3-oxobutanoate) can be condensed with anilines and subsequently cyclized to give 4-trifluoromethyl-2-quinolinones although only in poor yield. Heating these products with phosphoryl tribromide affords 2-bromo-4-(trifluoromethyl)quinolines which can be converted into 4-(trifluoromethyl)quinolines by redn., 4-trifluoromethyl-2-quinolinecarboxylic acids by permutational halogen/metal exchange followed by carboxylation, and 2-bromo-4-trifluoromethyl-3-quinolinecarboxylic acids by consecutive treatment with lithium diisopropylamide and dry ice. Debromination of the acids makes 4-trifluoromethyl-3-quinolinecarboxylic acids available. As at any time 2-trifluoromethyl-4-quinolinones may form instead of the expected 4-trifluoromethyl-2-quinolinone isomers , the structures have to be assigned on the basis of unequivocal NMR spectral criteria. [on SciFinder (R)]

Published in:
European Journal of Organic Chemistry, 11, 2115-2121
CAN 139:245879 27-17 Heterocyclic Compounds (One Hetero Atom) Institut de Chimie moleculaire et biologique,Ecole Polytechnique Federale,Lausanne,Switz. Journal 1434-193X written in English. 62-53-3 (Aniline); 95-53-4 (o-Toluidine); 106-49-0 (p-Toluidine); 108-44-1 (m-Toluidine); 371-40-4 (p-Fluoroaniline); 372-19-0 (m-Fluoroaniline); 536-90-3 (m-Anisidine) Role: RCT (Reactant), RACT (Reactant or reagent) (condensation reaction with Et trifluoroacetate); 372-31-6 (Ethyl 4,4,4-trifluoroacetoacetate) Role: RCT (Reactant), RACT (Reactant or reagent) (condensation reaction with anilines); 1701-23-1P; 1828-96-2P; 25199-84-2P; 328955-68-6P; 328956-08-7P; 404597-27-9P; 590372-17-1P; 590372-20-6P; 596845-28-2P; 596845-29-3P; 596845-30-6P; 596845-31-7P; 596845-32-8P; 596845-33-9P; 596845-34-0P; 596845-48-6P; 596845-49-7P; 596845-50-0P; 596845-51-1P; 596845-52-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and characterization of); 25199-77-3P; 155495-82-2P; 588702-67-4P; 596845-35-1P; 596845-36-2P; 596845-37-3P; 596845-38-4P; 596845-39-5P; 596845-40-8P; 596845-41-9P; 596845-42-0P; 596845-43-1P; 596845-44-2P; 596845-46-4P; 596845-47-5P; 596845-53-3P; 596845-54-4P; 596845-55-5P; 596845-56-6P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and characterization of); 7789-59-5 (Phosphoryl tribromide) Role: RCT (Reactant), RACT (Reactant or reagent) (reaction with trifluoromethylquinolines)
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 Record created 2006-03-03, last modified 2018-01-27

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