CASCADE RECYCLIZATION OF N-ARYLITACONIMIDES AS A NEW APPROACH TO THE SYNTHESIS OF POLYFUNCTIONAL OCTAHYDROQUINOLINES

Abstract

A new variant of Hantzsch reaction was developed for the synthesis of 1,2,3,4,5,6,7,8-octahydroquinolines on the basis of regioselective cascade recyclization of N-arylitaconimides in reactions with 3-aminocyclohex-2-enones. The mechanism of this domino process included С-nucleophilic addition of enaminone to the activated multiple bond of itaconimide and intramolecular transamidation with simultaneous recyclization of the intermediate.