Synthesis of quinolines, 2-quinolones, phenanthridines, and 6(5h)-phenanthridinones via palladium[0]-mediated Ullmann cross-coupling of 1-bromo-2-nitroarenes with beta-halo-enals, -enones, or -esters

Martin G Banwell; David W Lupton; Xinghua Ma; Jens Renner; Magne O Sydnes

doi:10.1021/ol0490375

Synthesis of quinolines, 2-quinolones, phenanthridines, and 6(5h)-phenanthridinones via palladium[0]-mediated Ullmann cross-coupling of 1-bromo-2-nitroarenes with beta-halo-enals, -enones, or -esters

Org Lett. 2004 Aug 5;6(16):2741-4. doi: 10.1021/ol0490375.

Authors

Martin G Banwell¹, David W Lupton, Xinghua Ma, Jens Renner, Magne O Sydnes

Affiliation

¹ Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia. mgb@rsc.anu.edu.au

PMID: 15281758
DOI: 10.1021/ol0490375

Abstract

Palladium[0]-mediated Ullmann cross-coupling of 1-bromo-2-nitrobenzene (1 R = H) and its derivatives with a range of beta-halo-enals, -enones, or -esters readily affords the corresponding beta-aryl derivatives, which are converted into the corresponding quinolines, 2-quinolones, phenanthridines, or 6(5H)-phenanthridinones on reaction with dihydrogen in the presence of Pd on C or with TiCl(3) in aqueous acetone. [reaction: see text]