Selective Synthesis of Quinolines and Indoles: Sulfur-Assisted or Selenium-Catalyzed Reaction of β-(2-Nitrophenyl)-α, β-unsaturated Ketones with Carbon Monoxide

A simple and selective synthetic method of quinolines and indoles by the reaction of beta-(2-nitrophenyl)-alpha, beta-unsaturated ketones with carbon monoxide was developed. When beta-(2-nitrophenyl)a, beta-unsaturated ketones were allowed to react with carbon monoxide and water in the presence of a stoichiometric amount of sulfur or a catalytic amount of selenium, the corresponding quinolines were produced in moderate-to-good yields. On the other hand, in the absence of water, the indoles were produced by the selenium-catalyzed reaction of the beta-(2-nitrophenyl)-alpha,beta-unsaturated ketones with carbon monoxide. (C) 2014 Wiley Periodicals, Inc.