Antidiabetische wirkstoffe, IV [1] trifluormethylsubstituierte 2-(4-toluidino)pyrimidine

Selective and Efficient Structural Elaboration of 2‐(Trifluoromethyl)quinolinones.

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Keywords: Bromine-lithium exchange / Ethyl 4,4,4-trifluoroacetoacetate / Heterocycles / Hydrogen-lithium exchange / Regioselectivity

The acid-catalyzed cyclization-condensation between anilines and ethyl 4,4,4-trifluoroacetoacetate affords 1,4-dihydro-2-trifluoromethyl-4H-4-quinolinones (1), which can easily be converted into 4-bromo-2-(trifluoromethyl)quinolines. An even greater variety of five-and six-membered nitrogen heterocycles has also been made available in such a way: 3-(trifluoromethyl)pyrroles, [7,8] 5-(trifluoromethyl)pyrazoles, [9,10] 3-(trifluoromethyl)-5-pyrrolinones, [11Ϫ15] 1,4-dihydro-2,6-bis(trifluoromethyl)pyridines, [16] 2-hetero-substituted 4-trifluoromethyl-6-pyridinones, [17Ϫ19] 2-amino-substituted 4-(trifluoromethyl)pyrimidines [20,21] or -pyrimidones [22Ϫ25] and (trifluoromethyl)quinolinones. From this building block, considerable numbers of 2-(trifluoromethyl)furans, [2] 2,5-dihydro-4-trifluoromethyl-2-furanones, [3] trifluoromethyl-substituted sugars [4,5] or cyclohexenones [6] and 4-trifluoromethyl-2-benzopyranones have been prepared.

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