New multicomponent method for the synthesis of polyhydrogenated pyrazino[1,2-a]quinolines

New multicomponent method for the synthesis of polyhydrogenated pyrazino[1,2-a]quinolines

A new one-pot method for the synthesis of 2,3,4,6,7,8,9,10-octahydro-1 H -pyrazino[1,2- a ]quinolines was developed based on a three-component reaction between methyl (3-oxopiperazin-2-ylidene)acetate, aromatic aldehydes, and cyclohexane-1,3-diones. It was shown by HPLC-MS analysis that this cascade...

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Veröffentlicht in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2016-05, Vol.52 (5), p.309-315
Hauptverfasser: Medvedeva, Svetlana M., Shikhlaliev, Khidmet S., Krysin, Mikhail Yu, Gotsak, Irina V.
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes
Chemistry
Chemistry and Materials Science
Cyclohexane
Methods
Organic Chemistry
Pharmacy
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Zusammenfassung:A new one-pot method for the synthesis of 2,3,4,6,7,8,9,10-octahydro-1 H -pyrazino[1,2- a ]quinolines was developed based on a three-component reaction between methyl (3-oxopiperazin-2-ylidene)acetate, aromatic aldehydes, and cyclohexane-1,3-diones. It was shown by HPLC-MS analysis that this cascade reaction involved a sequence of steps including condensation between 1,3-diketone and aldehyde, addition of heterocyclic enaminone as a C-nucleophile, and intramolecular heterocyclization.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-016-1876-9