Mild and efficient synthesis and base-promoted rearrangement of novel isoxazolo[4,5-b]pyridines

Abstract

An efficient method for the synthesis of isoxazolo[4,5-b]pyridines has been developed on the basis of readily available 2-chloro-3-nitropyridines via the intramolecular nucleophilic substitution of the nitro group as a key step. The previously unknown base-promoted Boulton–Katritzky rearrangement of isoxazolo[4,5-b]pyridine-3-carbaldehyde arylhydrazones into 3-hydroxy-2-(2-aryl[1,2,3]triazol-4-yl)pyridines was observed.

Keywords

• aromatic nitro compounds
• boulton–katritzky rearrangement
• isoxazolo[4,5-b]pyridines
• nucleophilic substitution
• 1,2,3-triazoles