Cascade recyclization of N-arylitaconimides as a new approach to the synthesis of polyfunctional octahydroquinolines

Cascade recyclization of N-arylitaconimides as a new approach to the synthesis of polyfunctional octahydroquinolines

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 e...

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Veröffentlicht in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2019-08, Vol.55 (8), p.748-754
Hauptverfasser: Kovygin, Yurii A., Shikhaliev, Khidmet S., Krysin, Mikhail Yu, Potapov, Andrei Yu, Ledenyova, Irina V., Kosheleva, Yevgeniya A., Vandyshev, Dmitriy Yu
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Cascade chemical reactions
Chemistry
Chemistry and Materials Science
Organic Chemistry
Pharmacy
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container_issue 8
container_start_page 748
container_title Chemistry of heterocyclic compounds (New York, N.Y. 1965)
container_volume 55
creator Kovygin, Yurii A.
Shikhaliev, Khidmet S.
Krysin, Mikhail Yu
Potapov, Andrei Yu
Ledenyova, Irina V.
Kosheleva, Yevgeniya A.
Vandyshev, Dmitriy Yu
description 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.
doi_str_mv 10.1007/s10593-019-02530-5
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subjects Cascade chemical reactions
Chemistry
Chemistry and Materials Science
Organic Chemistry
Pharmacy
title Cascade recyclization of N-arylitaconimides as a new approach to the synthesis of polyfunctional octahydroquinolines
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