Original synthesis of benzo[f]indole-4,9-dione derivatives using TDAE strategy
Abstract
A new series of 1-methyl-1H-benzo[f]indole-4,9-dione derivatives was prepared via a one-pot 'Sonogashira-Cyclization' reaction with propagylic alcohol in the presence of a palladium catalyst leading to regio-isomers of 2- and 3-(chloromethyl)-1-methyl-1H-benzo[f]indole-4,9-dione after chlorination. The reaction of the 2- and 3-(chloromethyl)-1-methyl-1H-benzo[f]indole-4,9-dione derivatives with various aldehydes and N-sulfonimides in the presence of TDAE under mild conditions led to the corresponding alcohols and N-sulfonamide derivatives in good yield. (C) 2015 Elsevier Ltd. All rights reserved.