Synthesis of Methoxy-2-quinolones via Pummerer-type Cyclization of N-Aryl-N-methyl-3-(phenylsulfinyl) propionamides.

…, M Sakagami, Y Goan, M Simakata, T Saitoh…

Index: Toda; Sakagami; Goan; Simakata; Saitoh; Horiguchi; Sano Chemical and Pharmaceutical Bulletin, 2000 , vol. 48, # 12 p. 1854 - 1861

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Citation Number: 7

Abstract

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, ...