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

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...

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Published inOrganic & biomolecular chemistry Vol. 2; no. 21; pp. 3134 - 3138
Main Authors Yamazaki, S, Morikawa, S, Iwata, Y, Yamamoto, M, Kuramoto, K
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 07.11.2004
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ROUTE
DIELS-ALDER
ASYMMETRIC-SYNTHESIS
ALPHA-ARYLATION
ALKYLATION
ENE REACTION
SUBSTITUTED OXINDOLES
2+2 CYCLOADDITION
GLYOXYLATE
CATALYSTS
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Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1477-0520
1477-0539
DOI:10.1039/b408728c