New Vistas in Quinoline Synthesis. -Ga/B-mediated reaction of anilines with nitriles allows a practical and rapid access to 2-aminoaryl ketones. Coupling of the latter with β-keto carbonyl compounds and sulfones provides a general method to prepare 2,3,4-trisubstituted quinolines. Reaction of the benzoxazinone (XIV) with keto sulfones also results in efficient formation of quinolines. -(ATECHIAN, S.; NOCK, N.; NORCROSS, R. D.; RATNI, H.; THOMAS, A. W.; VERRON, J.; MASCIADRI*, R.; Tetrahedron 63 (2007) 13, 2811-2823; Pharma Div., F. Hoffmann-La Roche AG, CH-4070 Basel, Switz.; Eng.) -Jannicke 27-122
A variety of arenes, including anilines, pyrroles, indoles, aminooxazoles, aminothiazoles, aminoquinolines, and aminopyridines, underwent regioselective Friedel−Crafts alkylation in neat hexafluoroacetone sesquihydrate in a broad range of temperatures, reaction times, and yields (2%−94%) depending strongly on the electron density of the substrate. Prior N,N-dibenzylation of aniline and 2-aminopyridine
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