Synthesis of Imidazopyridine- and Indole-Fused Azepinones via an Unusual Friedel–Crafts Alkylation of Chloroacetylated GBB Adducts
Abstract
A new Friedel-Crafts-type reaction involving the formation and ring expansion of spiro-β-lactam is discovered in the synthesis of imidazopyridine- and indole-fused azepinones. The Groebke-Blackburn-Bienaymé (GBB) reaction adducts undergo N-chloroacylation and Friedel-Crafts alkylation, which leads to polycyclic products in good yields. The DFT calculation indicates that in the Friedel-Crafts reaction spiralization at C-11 is kinetically more favorable than that directly at C-2. It is a novel rearrangement process for the synthesis of biologically interesting azepinone derivatives.
Fields of Study & Subjects
Synthesis and pharmacology of benzodiazepine derivatives
Synthesis and bioactivity of alkaloids
Catalytic C–H Functionalization Methods
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 10
- Pages
- 3167–3171
- Publication date
- 27 February 2026
- Language
- EN