One-Step Synthesis of Functionalized Pyrazolo[3,4-<i>b</i>]pyridines via Ring Opening of the Pyrrolinium Ion
Tanzilya S. Rizbayeva, Аndrey V. Smolobochkin, Almir S. Gazizov, Julia К. Voronina, Victor V. Syakaev, D. P. Gerasimova, О.А. Lodochnikova, Sergey V. Efimov, Vladimir V. Klochkov, А. Р. Бурилов, M. A. Pudovik
Abstract
Herein, we report a highly regioselective one-pot synthesis of pyrazolo[3,4- b ]pyridines via the reaction of 3-arylidene-1-pyrrolines with aminopyrazoles. The reaction proceeds through the sequential nucleophilic addition/electrophilic substitution/C–N bond cleavage and provides easy access to pyrazolo[3,4- b ]pyridine derivatives featuring a primary amino group. Moreover, the reaction can be terminated at the electrophilic substitution stage, thus providing convenient entry to the hardly accessible pyrazolopyrrolopyridine scaffold.
Topics & Concepts
RegioselectivityChemistryElectrophilePyridineRing (chemistry)Combinatorial chemistryNucleophilic substitutionNucleophileBond cleavageElectrophilic substitutionCleavage (geology)Nucleophilic additionSubstitution reactionLeaving groupMedicinal chemistryStereochemistryOrganic chemistryCatalysisMaterials scienceFracture (geology)Composite materialSynthesis and Reactivity of HeterocyclesMulticomponent Synthesis of HeterocyclesSynthesis and Characterization of Pyrroles