[Chemical and pharmaceutical research on pyran derivatives. X. Synthesis of 1-oxo-2-alkyl-3-dialkylamino-1H-naphtho[2,1b]pyrans].
When reaction of N,N-dialkyl-alpha-ethoxycarbonyl-alpha-alkylacetamides with beta-naphthol in the presence of phosphorus oxychloride was carried out in chlorobenzene at reflux, formation of 1-oxo-2-alkyl-3-dialkyl-amino-1H-naphtho[2,1-b]pyrans was achieved together with some other products whose structure was defined. Moreover, substitution of the 2 position of 1-oxo-3-dialkylamino-1H"naphtho[2,1-b]pyrans with chlorine or cyano group as well as the preparation of 1-thio-3-dialkylamino-1H-naphtho[2,1-b]pyrans was obtained by suitable chemical methods. Pharmacological screening of these compounds showed the lack of psychotropic activity of the corresponding 1-oxo-3-dialkylamino-1H-naphtho[2,1-b]pyrans.
D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis; D055598:Chemical Phenomena; D002621:Chemistry; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D008722:Methods; D051379:Mice; D011619:Psychotropic Drugs / Q000138:chemical synthesis; D011714:Pyrans / Q000138:chemical synthesis* / Q000494:pharmacology; D051381:Rats; D013055:Spectrophotometry, Infrared; D013329:Structure-Activity Relationship
D000894:Anti-Inflammatory Agents, Non-Steroidal; D011619:Psychotropic Drugs; D011714:Pyrans
Ricerche chimiche e farmacologiche su derivati piranici. Nota X. Sintesi di 1-oxo-2-alchil-3-dialchilammino-1H-nafto[2,1-b]pirani.