[Chemical and pharmacological research on derivatives of 1H-naphtho/2,1-b/pyran. V. Behavior of some 1-oxo-3-dialkylamino-1H-naphtho/2,1-b/pyrans substituted in the Mannich reaction].
1-Oxo-3-dialkylamino-1H-naphtho [2,1-b] pyrans substituted in positions 5, 8 or 9 with halogen, alkyl, alkoxycarbonyl, hydroxyl, methoxyl, by the Mannich reaction will yield the corresponding 2-dialkylamino-methyl derivatives when a correct amount of acetic acid is present in the reaction mixture. Excess acid will give rise to the formation of substituted 1-oxo-2-[(1'-oxy-3'-oxo-3'H-naphtho [2',1'-b']pyran-2'-yl)methyl]-3-dialkylamino-1H-naphtho [2,1-b] pyrans when the group in the 3 position is dimethylamino or N-pyrrolidyl. In a few cases Mannich bases were accompanied by an appreciable quantity of substituted 2,2'-methylenebis (1-oxo-3-dialkylamino-1H-naphtho-E12,1-B] PYRANS). Therefore, these compounds were synthesized with excellent yields by treating Mannich bases with acetic anhydride. The behavior of some compounds in the acidic hydrolysis was also considered. Some Mannich bases of 1-oxo-3-dialkylamino-9 methoxy-1H-naphtho-[2,1-b] pyrans showed a more specific anticonvulsant activity than the parent compounds.
D000818:Animals; D000927:Anticonvulsants / Q000138:chemical synthesis*; D004353:Drug Evaluation, Preclinical; D007202:Indicators and Reagents; D051379:Mice; D009281:Naphthalenes / Q000138:chemical synthesis; D011714:Pyrans / Q000138:chemical synthesis*; D051381:Rats
D000927:Anticonvulsants; D007202:Indicators and Reagents; D009281:Naphthalenes; D011714:Pyrans
Ricerche chimiche e farmacologiche su derivati del 1H-nafto [2,1-b] pirano. Nota V - Comportamento di alcuni 1-oxo-3-dialchilammino-1H-nafto [2,1-b] pirani sostituiti nella reazione di Mannich