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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-oxindoles†‡
K. Naresh Babu,Lakshmana K. Kinthada,Santanu Ghosh,Alakesh Bisai
Organic & Biomolecular Chemistry Pub Date : 08/24/2015 00:00:00 , DOI:10.1039/C5OB01670C
Abstract

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.

Graphical abstract: 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-oxindoles
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