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Paper | Regular issue | Vol 45, No. 12, 1997, pp.2395-2403
Published online, 1st January, 1970
DOI: 10.3987/COM-97-7958
Palladium Catalysed Coupling of Iodoquinolines and Acetylenes – A Novel Entry to the Pyrrolo[3,2,1-ij]quinoline Nucleus

Peter Blurton, Angela Brickwood, and Dashyant Dhanak*

*SmithKline Beecham Pharmaceuticals - UP1105, 1250 South Collegeville Road, Collegeville, PA 19426-0989, Denmark

Abstract

Treatment of 4-arylamino-8-iodoquinoline derivatives with propargyl alcohol and triethylamine in the presence of iodo(phenyl)bis(triphenylphosphine) palladium and copper (I) iodide gives 6-imino-substituted pyrrolo[3,2,1-ij]quinolines under mild conditions and in moderate yields. Catalytic hydrogenation over Lindlar’s catalyst affords functionalised 4H-pyrrolo[3,2,1-ij]quinolines in good yield.