New one-pot synthesis of 4-arylpyrazolo[3,4- <i>b</i> ]pyridin-6-ones based on 5-aminopyrazoles and azlactones
Vladislav Yu. Shuvalov, Ekaterina Yu Vlasova, Tatyana Yu. Zheleznova, Alexander S. Fisyuk
Abstract
An effective one-pot strategy was developed for the synthesis of 4-arylpyrazolo[3,4- b ]pyridin-6-ones from pyrazolo[3,4- b ]pyridin-6-ones, obtained by reacting 5-aminopyrazoles with 4-arylidene-2-phenyloxazol-5(4 H )-ones (azlactones) under solvent-free conditions, through subsequent elimination of a benzamide molecule in a superbasic medium ( t -BuOK/DMSO). The fluorescent properties of the synthesized compounds were studied. 4-Arylpyrazolo[3,4- b ]pyridin-6-ones luminesce in the region of 409–440 nm with a quantum yield of 0.09–0.23 when irradiated with UV light.
Topics & Concepts
ChemistryBenzamideYield (engineering)SolventQuantum yieldMoleculeCombinatorial chemistryFluorescenceMedicinal chemistryOrganic chemistryQuantum mechanicsMetallurgyMaterials sciencePhysicsSynthesis and Reactions of Organic CompoundsSynthesis and Biological EvaluationSynthesis and Characterization of Heterocyclic Compounds