Issue 2, 2010
From the journal:

Chemical Communications

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

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

* Corresponding authors

a Research Group SynBioC, Department of Organic Chemistry, Faculty of BioScience Engineering, Coupure Links 653, B-9000 Ghent, Belgium
E-mail: chris.stevens@ugent.be
Fax: +32 9264 6243
Tel: +32 9264 5950

b Institute of Chemistry and Environmental Protection, Jan Długosz University, Armii Krajowej 13/15 Ave, 42-201 Czestochowa, Poland
E-mail: crystal@cz.onet.pl
Fax: +48 34366 5322
Tel: +48 34366 5322

c Center of Molecular and Macromolecular Studies, Department of Heteroatom Chemistry, Polish Academy of Science, Sienkiewicza 112, 90-363 Lødz, Poland
E-mail: draj@bilbo.cbmm.lodz.pl
Fax: +48 42684 7126
Tel: +48 42680 3234

Abstract

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

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Article information

DOI
https://doi.org/10.1039/B906808B
Article type
Communication
Submitted
03 Apr 2009
Accepted
03 Nov 2009
First published
20 Nov 2009

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

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

A. De Blieck, K. G. R. Masschelein, F. Dhaene, E. Rozycka-Sokolowska, B. Marciniak, J. Drabowicz and C. V. Stevens, Chem. Commun., 2010, 46, 258 DOI: 10.1039/B906808B

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