Work

Selective Synthesis of Imidazo[4,5- f ]- and Imidazo[4,5- h ]quinoline N -Oxides via Base-Catalyzed Cyclization of ortho -Nitroalkylaminoquinolines

Year: 2025

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide We report an efficient base-catalyzed cyclization of readily available ortho -nitroalkylaminoquinolines for the synthesis of a series of imidazo[4,5- f ]quinoline and imidazo[4,5- h ]quinoline N -oxides. Using alkali metal alkoxides in anhydrous alcohol, we achieved good to excellent yields (up to 92%) of various N -oxides, allowing the corresponding N -oxidation products to be obtained selectively. The method is suitable for a wide range of substituents (except tertiary amines). This protocol opens a direct route to new, previously inaccessible imidazo[4,5]quinoline N -oxide derivatives, opening the way for future pharmacological studies, given their purine-like structures and potential therapeutic applications.

Source: ACS Omega

DOI: 10.1021/acsomega.5c09130