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RSC Advances | 2015

Novel synthesis and cytotoxic activity of 1,4-disubstituted 3-methylidene-3,4-dihydroquinolin-2(1H)-ones

Marlena Pięta; Jacek Kędzia; Anna Janecka; Dorota K. Pomorska; Marek Rozalski; Urszula Krajewska; Tomasz Janecki

A novel, efficient synthesis of 1,4-disubstituted 3-methylidene-3,4-dihydrodihydroquinolin-2(1H)-ones was accomplished via a three step reaction sequence comprising N-alkylation of 3-diethoxyphosphorylquinolin-2(1H)-one, Michael addition of various Grignard reagents to N-alkylated 3-diethoxyphosphorylquinolin-2(1H)-ones and a Horner–Wadsworth–Emmons reaction of the obtained adducts with formaldehyde. Effective synthesis of the starting 3-diethoxyphosphorylquinolin-2(1H)-one was also developed. Furthermore, the obtained 3-methylidene-3,4-dihydroquinolin-2(1H)-ones were evaluated for their cytotoxic activity.


Acta Crystallographica Section C-crystal Structure Communications | 2008

trans-(1R,2R)-1-benzyl-2-phenylcyclopropanecarboxylic acid.

Henryk Krawczyk; Katarzyna Wąsek; Jacek Kędzia; Jakub Wojciechowski; Wojciech M. Wolf

The cyclopropane ring of the title compound, C17H16O2, shows a high level of substituent-induced bond-length asymmetry. The carboxyl group adopts a conformation that prompts electron-density transfer from the ring towards the carbonyl pi system.


Synthesis | 2009

Michael Additions to ActivatedVinylphosphonates

Tomasz Janecki; Jacek Kędzia; Tomasz Wąsek


Organic and Biomolecular Chemistry | 2008

A general stereoselective method for the synthesis of cyclopropanecarboxylates. A new version of the homologous Horner–Wadsworth–Emmons reaction

Henryk Krawczyk; Katarzyna Wąsek; Jacek Kędzia; Jakub Wojciechowski; Wojciech M. Wolf


Tetrahedron-asymmetry | 2006

Highly enantioselective synthesis of α-methylene-δ-valerolactones by an asymmetric Michael reaction

Henryk Krawczyk; Marcin Śliwiński; Jacek Kędzia; Jakub Wojciechowski; Wojciech M. Wolf


Tetrahedron Letters | 2006

New, diastereoselective synthesis of 1-alkyl-5-alkylidene-3-methylidenepyrrolidin-2-ones

Anna Albrecht; Jacek Kędzia; Jacek F. Koszuk; Edyta Warzycha; Tomasz Janecki


Tetrahedron-asymmetry | 2007

Asymmetric synthesis of enantiomerically pure 7-isopropenyl-4a-methyl-3-methyleneoctahydrochromen-2-ones

Henryk Krawczyk; Marcin Śliwiński; Jacek Kędzia; Jakub Wojciechowski; Wojciech M. Wolf


Tetrahedron-asymmetry | 2006

Enantiomerically pure P-chiral dicyclohexylammonium 2-(phosphinyl)acrylates as new Michael acceptors. Enantioselective synthesis of α-methylene-δ-valerolactones

Henryk Krawczyk; Marcin Śliwiński; Jacek Kędzia


Tetrahedron-asymmetry | 2010

An efficient approach to the synthesis of enantiomerically pure trans-1-amino-2-(hydroxymethyl)cyclopropanephosphonic acids

Katarzyna Wąsek; Jacek Kędzia; Henryk Krawczyk


Synlett | 2005

Base-Catalyzed Ethanolysis of α-Diethoxyphosphoryl-γ-lactones: A Facile Synthesis of Cyclopropanecarboxylates

Henryk Krawczyk; Katarzyna Wąsek; Jacek Kędzia

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