The present study provides an efficient strategy for the preparation of novel N-substituted-4-methyl-quinolin-1(2H)-one derivatives via two-step Ugi/Heck reaction. The procedure is based on the Ugi coupling between 2-bromoanilines, various aromatic aldehydes, vinylacetic acid, and isocyanides, and then intramolecular Heck reaction, which leads to the formation of the title compounds in good yields.
2-Chloro-3-formyl quinoline has been applied as an aldehyde moiety in the Groebke-Blackburn-Bienaymé multi-component reaction with isocyanides, 2-aminoazines, and 2-aminoazole to afford the desired adducts which are amenable for further cyclization on the basis of Ullmann-type coupling. The copper iodide-mediated intramolecular C-N bond formation in the second step gave an easy access to a series of imidazo[4[Formula: see text],5[Formula: see text]:4,5]pyrrolo[2,3-b]quinoline derivatives in moderate to good yields.
Berzelius failed to make use of Faraday's electrochemical laws in his laborious determination of equivalent weights.