Regioselective Ortho -Azidation of Anilines via Quinone Imine Ketals: A One-Pot Approach to Proton Pump Inhibitors
Abstract
Here, we demonstrated a metal-free, Brønsted acid-catalyzed, regioselective nondirected C–H activation reaction that efficiently achieves ortho -functionalization of p -anisidines via quinone imine ketals. Besides streamlining the synthesis of ortho -azidated anilines, our method is scalable and exhibits a high tolerance to various functional groups. Control experiments and comprehensive 2D NMR analysis confirmed the ortho -selectivity. The protocol was also adapted to synthesize difficult diaminated arenes and successfully used to produce marketed proton-pump inhibitors, Ufiprazole and Omeprazole.
Fields of Study & Subjects
Catalytic C–H Functionalization Methods
Synthesis and Catalytic Reactions
Radical Photochemical Reactions
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Volume
- 91
- Issue
- 5
- Pages
- 1912–1919
- Publication date
- 28 January 2026
- Language
- EN