Sequential alkylation/heterocyclization of beta-(2-aminophenyl)-alpha,beta-ynones promoted by electrogenerated carbanions: A new approach to functionalized 4-alkylquinolines

Electrolysis in a divided cell (nitroalkanes or methanol, in the absence of solvent and supporting electrolyte, as catholite) gave functionalized 4-alkylquinolines in moderate to high yields through a sequential alkylative heterocyclization of beta-(2-aminophenyl)-alpha,beta-ynones. The sequential alkylative heterocyclization process can be extended to the reaction of beta-(2-aminophenyl)-alpha,beta-ynones with 1,3-dicarbonyls by galvanostatic electrolysis of these latter derivatives in a tetraethyl ammonium tetrafluoroborate-N,N-dimethylformamide solution.