[HTML][HTML] Divergent Pathways for Reactions of 3-Formylchromone with Cyclic Secondary Amines in Alcoholic Media

KS Korzhenko, DV Osipov, VA Osyanin… - …, 2019 - thieme-connect.com
KS Korzhenko, DV Osipov, VA Osyanin, YN Klimochkin
SynOpen, 2019thieme-connect.com
Reaction of 3-formylchromone with cyclic secondary amines in methanol results in (E)-2-
methoxy-3-(R 2 N-methylene) chroman-4-ones, while use of ethanol leads to (E)-2-
morpholino-3-(morpholinomethylene) chroman-4-one or enaminoketones as dihydropyran
ring-opening products. The solubility of the formed products in alcoholic media is postulated
to be a key factor that determines the reaction pathway.
Reaction of 3-formylchromone with cyclic secondary amines in methanol results in (E)-2-methoxy-3-(R2N-methylene)chroman-4-ones, while use of ethanol leads to (E)-2-morpholino-3-(morpholinomethylene)chroman-4-one or enaminoketones as dihydropyran ring-opening products. The solubility of the formed products in alcoholic media is postulated to be a key factor that determines the reaction pathway.
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