Brønsted-acid-catalyzed selective Friedel–Crafts monoalkylation of isatins with indolizines in water. Issue 37 (18th September 2020)

• Record Type: Journal Article
• Authors: Guidotti, Bruno Boni; da Silva, Thiago Sabino; Menezes Correia, José Tiago; Coelho, Fernando
• Is Part Of: Organic & biomolecular chemistry. Volume 18:Issue 37(2020)
• Page Start: 7330
• Page End: 7335
• Publication Date: 2020-09-18
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d0ob01714k
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Controlled Friedel–Crafts monoalkylations of indolizines with isatins have been achieved by using water as the solvent. This is the first organocatalyzed indolizine 1, 2-addition reported. Abstract : 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.