The C-3 acylation of 1-hydroxyindoles. Issue 8 (22nd February 2017)

• Record Type: Journal Article
• Authors: Chirkova, Zhanna V.; Kabanova, Mariya V.; Filimonov, Sergey I.; Abramov, Igor G.; Samet, Alexander V.; Stashina, Galina A.; Suponitsky, Kyrill Yu.
• Is Part Of: Tetrahedron letters. Volume 58:Issue 8(2017)
• Page Start: 755
• Page End: 757
• Publication Date: 2017-02-22
• Subjects: 1-Hydroxyindoles -- 3-Acyl-1-hydroxyindole-5, 6-dicarbonitriles -- 3-Acyl-1-acyloxyindole-5, 6-dicarbonitriles -- Boron trifluoride etherate; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.01.025
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: The first direct C-3 acylation of 1-hydroxyindole derivatives was accomplished. Aliphatic anhydrides were used as acylating agents and BF3 ·Et2 O as a promoter. Intermediate 3-acyl-1-acyloxyindoles were readily hydrolyzed to 3-acyl-1-hydroxyindoles. Abstract: The C-3 acylation of 1-hydroxyindole derivatives with aliphatic acid anhydrides was accomplished in high yields using BF3 ·Et2 O as a promoter, affording the corresponding 3-acyl-1-acyloxyindoles which in turn were readily hydrolyzed to the corresponding 3-acyl-1-hydroxyindole derivatives.