Michael Initiated Ring Closure (MIRC) reaction on in situ generated benzylidenecyclohexane-1,3-diones for the construction of chromeno[3,4-b]quinoline derivatives

One-pot synthesis of chromeno[3,4-b]quinoline derivatives have been achieved in good yields through Michael Initiated Ring Closure (MIRC) by employing three-component condensation of aromatic aldehydes, 3-aminocoumarins, and cyclic 1,3-diketones in the presence of catalytic amount of p-toluenesulfonic (p-TSA) acid in ethanol under reflux condition. The salient features of this protocol are: simple reaction procedure, shorter reaction time, good yields, avoidance of aqueous work-up, and column-chromatographic separation. The merit of this process is highlighted by its high bond efficiency of producing three new bonds and one stereocenter in a single operation. (C) 2012 Elsevier Ltd. All rights reserved.