CASCADE RECYCLIZATION OF <i>N</i>-ARYLITACONIMIDES AS A NEW APPROACH TO THE SYNTHESIS OF POLYFUNCTIONAL OCTAHYDROQUINOLINES

Authors

  • Юрий А. Ковыгин Voronezh State University, 1 Universitetskaya Sq., Voronezh 394018, Russia
  • Хидмет С. Шихалиев Voronezh State University, 1 Universitetskaya Sq., Voronezh 394018, Russia
  • Михаил Ю. Крысин Voronezh State University, 1 Universitetskaya Sq., Voronezh 394018, Russia
  • Андрей Ю. Потапов Voronezh State University, 1 Universitetskaya Sq., Voronezh 394018, Russia
  • Ирина В. Леденёва Voronezh State University, 1 Universitetskaya Sq., Voronezh 394018, Russia
  • Евгения А. Кошелева Voronezh State University, 1 Universitetskaya Sq., Voronezh 394018, Russia
  • Дмитрий Ю. Вандышев Voronezh State University, 1 Universitetskaya Sq., Voronezh 394018, Russia

DOI:

https://doi.org/10.1007/5050

Keywords:

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

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.

Author Biography

Михаил Ю. Крысин, Voronezh State University, 1 Universitetskaya Sq., Voronezh 394018, Russia

профессор кафедры органической химии

Downloads

Published

2019-08-14

Issue

Vol. 55 No. 8 (2019)

Section

Original Papers