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Start Over Author "Satoshi Morikawa" Publisher royal society of chemistry (rsc)
1 results on '"Satoshi Morikawa"'

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

Author

Satoshi Morikawa, Shoko Yamazaki, Kaori Kuramoto, Yuko Iwata, and Machiko Yamamoto

Subjects
Organic Chemistry, Biochemistry, chemistry.chemical_compound, Malonate, chemistry, Intramolecular force, Michael reaction, Organic chemistry, Oxindole, Lewis acids and bases, Physical and Theoretical Chemistry, Methylene, Benzofuran, Friedel–Crafts reaction
Abstract

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.

Published
2004
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