Expedient one-pot synthesis of indolo[3,2-c]isoquinolines via a base-promoted N-alkylation/tandem cyclization

A transition metal-free, one-pot protocol has been developed for the synthesis of 11H-indolo[3,2c]isoquinolin-5-amines via the atom economical annulation of ethyl (2-cyano-phenyl)carbamates and 2-cyanobenzyl bromides. This method proceeds via sequential N-alkylation and base-promoted cyclization. Optimization data, substrate scope, mechanistic insights, and photoluminescence properties are discussed. (C) 2015 Elsevier Ltd. All rights reserved.