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Chem. Commun., 2010, 46, 258 - 260, DOI: 10.1039/b906808b

One-pot tandem 1,4–1,2-addition of phosphites to quinolines

Ann De Blieck, Kurt G. R. Masschelein, Fréderic Dhaene, Ewa Rozycka-Sokolowska, Bernard Marciniak, Jozef Drabowicz and Christian V. Stevens

Trialkyl and silylated dialkyl phosphites were evaluated as phosphorus nucleophiles for the addition to quinolines in a strong acidic medium allowing consecutive 1,4- and 1,2-addition breaking up the aromatic stabilisation, thereby leading to 2,4-diphosphono-1,2,3,4-tetrahydroquinolines in one single reaction step in moderate to good yields (2–84%).

Graphical abstract image for this article (ID: b906808b)