[Chemical and pharmacological research on pyran derivatives. VIII. Synthesis of 2-dialkylamino-7-methoxychromones and derivatives].
2-Dialkylamino-7-methoxychromones were prepared by reaction of a m-methoxyphenol with N,N-dialkylethoxycarbonylacetamides in the presence of phosphorus oxychloride. Treatment of such compounds with 57% hydriodic acid resulted in the formation of the corresponding 7-hydroxy derivatives. These latter, treated with dialkylamines and formaldehyde, were transformed into the 8-dialkylaminomethyl derivatives. On the other hand the reaction of 2-dialkylamino-7-methoxychromones with morpholine and formaldehyde, in the presence of acetic acid, led to the formation of the corresponding 3-morpholinomethyl derivatives. Pharmacological investigation showed that 2-dialkylamino-7-hydroxy-chromones were without effect, whereas all other compounds tested had a clear, but generally weak, CNS stimulant activity.
D000818:Animals; D002490:Central Nervous System / Q000187:drug effects; D002867:Chromones / Q000138:chemical synthesis* / Q000494:pharmacology; D007202:Indicators and Reagents; D051379:Mice; D011714:Pyrans / Q000138:chemical synthesis* / Q000494:pharmacology; D051381:Rats; D012106:Research
D002867:Chromones; D007202:Indicators and Reagents; D011714:Pyrans
Ricerche chimiche e farmacologiche su derivati piranici. Nota VIII - Sintesi di 2-dialchilammino-7-metossicromoni e derivati