通过N-芳基-N-甲基-3-(苯基亚磺酰基)丙酰胺的普默勒尔型环化反应合成甲氧基-2-喹诺酮类化合物。
Synthesis of methoxy-2-quinolones via pummerer-type cyclization of N-aryl-N-methyl-3-(phenylsulfinyl)propionamides.
作者信息
Toda J, Sakagami M, Goan Y, Simakata M, Saitoh T, Horiguchi Y, Sano T
机构信息
Showa Pharmaceutical University, Machida, Tokyo, Japan.
出版信息
Chem Pharm Bull (Tokyo). 2000 Dec;48(12):1854-61. doi: 10.1248/cpb.48.1854.
The thionium ions 10 generated by Pummerer reaction of N-aryl-N-methyl-3-(phenylsulfinyl)propionamides 4 caused not only an electrophilic cyclization reaction producing 2-quinolones 8, but also the formation of the vinyl sulfides 5 and 6 in favor of the latter reaction. On the other hand, the treatment of the vinyl sulfides 5 and 6 with p-toluenesulfonic acid induced cyclization to afford the 2-quinolones 8 in excellent to moderate yields, depending on the electronic properties of the aromatic ring, thus providing a convenient method for the synthesis of methoxy-2-quinolones.
N-芳基-N-甲基-3-(苯基亚磺酰基)丙酰胺4经普默勒尔反应生成的硫鎓离子10不仅引发亲电环化反应生成2-喹诺酮8，还生成了乙烯基硫醚5和6，且更倾向于后一种反应。另一方面，用对甲苯磺酸处理乙烯基硫醚5和6会引发环化反应，根据芳环的电子性质，以优异至中等的产率得到2-喹诺酮8，从而为甲氧基-2-喹诺酮的合成提供了一种简便方法。
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