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Synfacts 2008(9): 0911-0911  
DOI: 10.1055/s-2008-1078617
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Pd-Catalyzed Synthesis of 4-Quinolones

Contributor(s): Victor Snieckus, Jignesh J. Patel
J. Huang*, Y. Chen, A. O. King, M. Dilmeghani, R. D. Larsen, M. M. Faul
Amgen Inc., Thousand Oaks, USA
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Publication History

Publication Date:
22 August 2008 (online)

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Significance

Reported here is a one-pot synthesis of 2-substituted 4-quinolones via Pd-catalyzed C-N coupling of primary amides with 2-bromo­acetophenones followed by base-induced intramolecular cyclization. Among the screened base/solvent combinations, NaOt-Bu in dioxane was found to be the optimal choice in the presence of Xantphos as ligand. Use of Cs2CO3 in polar solvents (DMF, NMP) gave mixtures of products and poor yields.