Brønsted-acid-catalyzed selective Friedel-Crafts monoalkylation of isatins with indolizines in water.

Org Biomol Chem

Laboratory of Synthesis of Natural Products and Drugs - Institute of Chemistry, University of Campinas, Rua Monteiro Lobato, S/N, 13083-970, Campinas, São Paulo, Brazil.

Published: September 2020

The controlled mono-addition of indolizines to isatins under very mild conditions is described. The reaction occurs in water using diphenylphosphate as the catalyst, which is dramatically accelerated by surfactant addition. 3-Hydroxy-3-indolizinyl-2-oxindole scaffolds were synthesized in up to >99% yield. Notably, in organic solvents only bis-addition products were observed.

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Source
http://dx.doi.org/10.1039/d0ob01714kDOI Listing

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