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

Юрий А. Ковыгин, Хидмет С. Шихалиев, Михаил Ю. Крысин, Андрей Ю. Потапов, Ирина В. Леденёва, Евгения А. Кошелева, Дмитрий Ю. Вандышев
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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.

Keywords


aminocyclohexenones; itaconimides; octahydroquinolines; cascade reactions; Hantzsch reaction.

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