A Lewis acid-promoted cyclization of ethenetricarboxylate derivative aromatic compounds. Novel syntheses of oxindoles and benzofuranones via Friedel-Crafts intramolecular Michael addition.

نویسندگان

  • Shoko Yamazaki
  • Satoshi Morikawa
  • Yuko Iwata
  • Machiko Yamamoto
  • Kaori Kuramoto
چکیده

A novel cyclization reaction of ethenetricarboxylate derivative aromatic compounds in the presence of various Lewis acids gave benzo-annulated cyclic compounds such as oxindole and benzofuran derivatives via Friedel-Crafts intramolecular Michael addition in high yields. For example, the reaction of diethyl 2-[(N-methyl-N-phenylcarbamoyl)methylene]malonate (1a) in the presence of ZnCl2 at room temperature gave diethyl 2-(1-methyl-2-oxoindolin-3-yl)malonate (2a) in 98% yield. The reactions also proceeded with a catalytic amount of a Lewis acid such as AlCl3, ZnCl2, ZnBr2, Sc(OTf)3, or InBr3.

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عنوان ژورنال:
  • Organic & biomolecular chemistry

دوره 2 21  شماره 

صفحات  -

تاریخ انتشار 2004