Synthesis of Chromone‐Containing Allylmorpholines through a Morita–Baylis–Hillman‐Type Reaction

The first example of an unusual addition of chromone‐substituted acrylic acid to enamines is described. The process shows high versatility concerning both enamines and chromones. The reaction is catalyzed by tertiary amines and is highly likely of Morita–Baylis–Hillman‐type. The described compounds...

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Veröffentlicht in:European journal of organic chemistry 2018-12, Vol.2018 (45), p.6304-6313
Hauptverfasser: Chernov, Nikita M., Shutov, Roman V., Barygin, Oleg I., Dron, Mikhail Y., Starova, Galina L., Kuz'mich, Nikolay N., Yakovlev, Igor P.
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Sprache:eng
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Zusammenfassung:The first example of an unusual addition of chromone‐substituted acrylic acid to enamines is described. The process shows high versatility concerning both enamines and chromones. The reaction is catalyzed by tertiary amines and is highly likely of Morita–Baylis–Hillman‐type. The described compounds show combined moderate inhibitory action on BChE and antagonism towards NMDA receptors which makes them a perspective group for the development of anti‐Alzheimer drugs. An unusual addition of enamines to chromone‐substituted acrylic acid is an efficient and versatile method of synthesis of allylamine derivatives. The reaction is catalyzed by amines and is highly likely of Morita–Baylis–Hillman‐type. The described compounds show combined moderate inhibitory action on BChE and antagonism towards NMDA receptors
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201801159