4.6 Article

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

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 18, Issue 37, Pages 7330-7335

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d0ob01714k

Keywords

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Funding

  1. Coordenacao de Aperfeicoamento de Pessoal de Nivel Superior - Brasil (CAPES) [001]
  2. Brazilian National Council for Science and Development (CNPq) [307840/2014-0, 422890-2016-2, 301330/2018-2]
  3. FAPESP [2013/07600-3, 2018/02611-0, 2012/218090]
  4. CAPES

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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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