Roma G, Vigevani E, Mazzei M, Ermili A, Ambrosini A, Passerini N
Farmaco Sci. 1978 Nov;33(11):822-37.
Reaction of N,N-dialkylethoxycarbonylacetamides with 1-methyl-2-naphthol, in the presence of phosphorus oxychloride, gave rise to the formation of 2-dialkylamino-4-oxo-10-methyl-4H-naphtho[2,3-b] pyrans through the preliminary attack of the amide-phosphorus oxychloride reactant at the phenolic hydroxyl and cyclization at position 3 of the naphthalene moiety. However when (N-alkyl,N-phenyl)ethoxycarbonylacetamides were used in the reaction an ortho position of the N-phenyl group was involved in the cyclization and 1-alkyl-2(1'-methyl-2'-naphthoxy)-4-quinolones were achieved. Pharmacological investigation showed that some naphtho[2,3-b]pyran derivatives have neurotropic activity of the sedative, anticonvulsant and antidepressant type very similar to that shown by previously studied 1-oxo-3-dialkylamino-1H-naphtho[2,1-b]pyrans (5).
在三氯氧磷存在下，N,N - 二烷基乙氧羰基乙酰胺与1 - 甲基 - 2 - 萘酚反应，通过酰胺 - 三氯氧磷反应物先对酚羟基进行进攻，然后在萘部分的3位环化，生成2 - 二烷基氨基 - 4 - 氧代 - 10 - 甲基 - 4H - 萘并[2,3 - b]吡喃。然而，当反应中使用（N - 烷基，N - 苯基）乙氧羰基乙酰胺时，N - 苯基的邻位参与环化，得到1 - 烷基 - 2(1'-甲基 - 2'-萘氧基)-4 - 喹诺酮。药理研究表明，一些萘并[2,3 - b]吡喃衍生物具有与先前研究的1 - 氧代 - 3 - 二烷基氨基 - 1H - 萘并[2,1 - b]吡喃（5）所示的非常相似的镇静、抗惊厥和抗抑郁类型的亲神经活性。
