Highly chemoselective synthesis of dimeric 2-oxindoles with a C-3/C-5′ linkage via Friedel-Crafts alkylations of 2-oxindoles with 3-hydroxy-2-oxindolesThis paper is dedicated to Professor T. K. Chandrasekhar on the occasion of his 60th Birthday.Electronic supplementary information (ESI) available: Experimental procedures, characterization data, NMR spectra. CCDC 1056290 and 1406284. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5ob01670c

Simple and convenient Lewis acid-catalyzed Friedel-Crafts alkylations of 2-oxindoles as electron rich aromatics with 3-hydroxy-2-oxindoles as electron deficient partners have been developed. The reaction afforded a variety of dimeric 2-oxindoles with a C-3/C-5′ linkage having an all-carbon quaternar...

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Main Authors: Babu, K. Naresh, Kinthada, Lakshmana K, Ghosh, Santanu, Bisai, Alakesh
Format: Article
Language:English
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Summary:Simple and convenient Lewis acid-catalyzed Friedel-Crafts alkylations of 2-oxindoles as electron rich aromatics with 3-hydroxy-2-oxindoles as electron deficient partners have been developed. The reaction afforded a variety of dimeric 2-oxindoles with a C-3/C-5′ linkage having an all-carbon quaternary center at the pseudobenzylic position in high yields. An expeditious approach to a variety of dimeric 2-oxindoles with a C-3/C-5′ linkage sharing an all-carbon quaternary center at the pseudobenzylic position has been developed via Lewis acid-catalyzed F-C alkylations.
ISSN:1477-0520
1477-0539
DOI:10.1039/c5ob01670c