Aminophthalimide as a Protected Nitrogen Source for N-Insertion to Indenones
Abstract
Nitrogen scanning is central to medicinal chemistry, yet N-positional variants and N–H analogues often require de novo synthesis. We report a nitrene-based, two-step one-pot formal N–H insertion into indenones to access isoquinolinones. N -Aminophthalimide, activated by PIDA, aziridinates the C═C bond and the resulting N-NPhth intermediate undergoes acid-promoted rearrangement in one pot. The method tolerates diverse substrates, including previously unreactive 2-alkyl and strongly electron-poor enones, and enables easy deprotection to N–H isoquinolinones.
Fields of Study & Subjects
Synthesis and Catalytic Reactions
Catalytic C–H Functionalization Methods
Advanced Synthetic Organic Chemistry
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 15
- Pages
- 4772–4776
- Publication date
- 8 April 2026
- Language
- EN