Selective and efficient structural elaboration of 2-(trifluoromethyl)quinolinones

The acid-catalyzed cyclization-condensation between anilines and Et 4,4,4-trifluoroacetoacetate affords 1,4-dihydro-2-trifluoromethyl-4H-4-quinolinones, which can easily be converted into 4-bromo-2-(trifluoromethyl)quinolines. These undergo halogen/metal exchange, generating 2-trifluoromethyl-4-quinolyllithiums, when treated with butyllithium, and hydrogen/metal exchange, generating 4-bromo-2-trifluoromethyl-3-quinolyllithiums, when treated with lithium diisopropylamide. Trapping of the latter intermediates provides 3-functionalized products that may be further elaborated by electrophilic substitution of the bromine atom. A few unexpected findings resulted from these investigations, the most noteworthy being an unprecedented buttressing effect and a counterintuitive halogen reactivity. [on SciFinder (R)]

Published in:
European Journal of Organic Chemistry, 8, 1576-1588
CAN 139:214307 27-17 Heterocyclic Compounds (One Hetero Atom) Institut de Chimie moleculaire et biologique,Ecole Polytechnique Federale,Lausanne,Switz. Journal 1434-193X written in English. 587885-95-8P Role: BYP (Byproduct), PREP (Preparation) (prepn. and reactions of 2-(trifluoromethyl)quinolines); 62-53-3 (Aniline); 106-49-0 (p-Toluidine); 334-88-3 (Diazomethane); 348-54-9 (2-Fluoroaniline); 371-40-4 (4-Fluoroaniline); 372-19-0 (3-Fluoroaniline); 372-31-6 (Ethyl 4,4,4-trifluoroacetoacetate); 461-82-5 (4-(Trifluoromethoxy)aniline); 536-90-3 (m-Anisidine); 615-36-1 (2-Bromoaniline); 615-43-0 (2-Iodoaniline) Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. and reactions of 2-(trifluoromethyl)quinolines); 18706-25-7P; 18706-27-9P; 18706-39-3P; 31008-96-5P; 31009-33-3P; 39975-59-2P; 39975-60-5P; 83842-55-1P; 89446-63-9P; 123638-04-0P; 587885-82-3P; 587885-83-4P; 587885-84-5P; 587885-85-6P; 587885-86-7P; 587885-87-8P; 587885-88-9P; 587885-89-0P; 587885-90-3P; 587885-91-4P; 587885-92-5P; 587885-93-6P; 587885-94-7P; 587886-03-1P; 587886-06-4P; 587886-07-5P; 587886-08-6P; 587886-09-7P; 587886-10-0P; 587886-11-1P; 587886-12-2P; 587886-14-4P; 587886-15-5P; 587886-16-6P; 587886-17-7P; 587886-19-9P; 587886-20-2P; 587886-21-3P; 587886-22-4P; 587886-23-5P; 587886-25-7P; 587886-31-5P; 587886-32-6P; 587886-33-7P; 587886-34-8P; 587886-35-9P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and reactions of 2-(trifluoromethyl)quinolines); 324-33-4P; 347-42-2P; 1860-47-5P; 18706-40-6P; 31009-06-0P; 31009-07-1P; 176722-68-2P; 587885-96-9P; 587885-97-0P; 587885-98-1P; 587885-99-2P; 587886-00-8P; 587886-01-9P; 587886-02-0P; 587886-04-2P; 587886-05-3P; 587886-13-3P; 587886-18-8P; 587886-24-6P; 587886-26-8P; 587886-27-9P; 587886-28-0P; 587886-29-1P; 587886-30-4P; 587886-36-0P; 587886-37-1P; 587886-38-2P; 587886-39-3P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and reactions of 2-(trifluoromethyl)quinolines)
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 Record created 2006-03-03, last modified 2018-01-27

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