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; Christian V. Stevens

doi:10.1039/B906808B

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Chemical Communications

Issue 2, 2010

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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

Chem. Commun., 2010, 46, 258-260

DOI: 10.1039/B906808B
Received 03 Apr 2009, Accepted 03 Nov 2009
First published on the web 20 Nov 2009

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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%).

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Experimental procedures and data of molecules 5a–5j and 12
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Articles By

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

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Chemical Communications

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

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