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Paper | Special issue | Vol 67, No. 1, 2006, pp.269-289
Published online, 23rd August, 2005
DOI: 10.3987/COM-05-S(T)25
A Lewis-Acid Catalyzed Synthesis of Substituted Oxindole Derivatives

Shoko Yamazaki,* Machiko Yamamoto, and Satoshi Morikawa

*Department of Chemistry, Nara University of Education, Takabatake-cho, Nara 630-8528, Japan

Abstract

Lewis acid-catalyzed cyclization of various 2-(N-arylcarbamoyl)-methylenemalonates to give nitrogen-containing benzo-annelated heterocycles was investigated in terms of selectivity. Reaction of substrates with various alkyl groups on nitrogen proceeded to give oxindole derivatives. Cyclization reaction of diester-amides of MeO and halogen-substituted anilines in the presence of catalytic Lewis acid (ZnCl2, SnCl4, AlCl3, Zn(OTf)2, Sc(OTf)3, etc.) gave oxindoles in high yields. Interesting regioselectivity was observed for meta-halogen substrates. Dimethoxyisoquinoline analogs were also obtained by this reaction using a catalytic Lewis acid.