No abstract

A new one-pot reaction for the regioselective construction of a six-membered fused N-heterocyclic ring leading to isoquinolones under Pd/C-Cu catalysis is described.

SummaryA two step synthesis of 2-alkynyl-4-arylquinolines has been accomplished via Pd/C-mediated regioselective C-2 alkynylation of 2,4-dichloroquinoline in water followed by Suzuki coupling at C-4 of the resulting 4-chloro derivative.

Pd/C catalisa a reação de acoplamento entre 2,4-diiodoquinolina e alquinos terminais em água, proporcionando uma síntese prática, de uma etapa, de 2,4-dialquinilquinolinas. Uma série de derivados de quinolinas relacionadas foi preparada em bons a excelentes rendimentos, usando esta metodologia baseada em água. O uso de outros catalisadores de paládio e solventes foi examinado e o mecanismo de reação discutido.Pd/C facilitated dual C-C bond forming reaction between 2,4-diiodoquinoline and terminal alkynes in water providing a practical and one-step synthesis of 2,4-dialkynylquinolines. A number of related quinoline derivatives were prepared in good to excellent yields using this water-based methodology. The use of other palladium catalysts and solvents was examined and the mechanism of the reaction has been discussed.

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Sonogashira coupling of 2-chloroquinoline (I) with terminal alkynes (II) proceeds smoothly in aqueous solution to afford 2-alkynylquinolines (III). The analogous cross-coupling of 2,4-dichloroquinoline (IV) proceeds regioselectively at position 2. -(REDDY, E. A.; BARANGE, D. K.; ISLAM, A.; MUKKANTI, K.; PAL*, M.; Tetrahedron 64 (2008) 30-31, 7143-7150; Discovery Res., Dr. Reddy's Lab. Ltd., Hyderabad 500 049, India; Eng.) -Mischke 50-139