Add time:08/02/2019         Source:sciencedirect.com

This review covers the carbon-nitrogen (C–N) bond forming reactions of pyridines that include both electrophilic as well as nucleophilic substitution reactions. The electrophilic reactions, such as nitration and nitrosation, include both the classical methods and their recent modifications. Nucleophilic reactions include Chichibabin and related amination reactions, with hydrogen as the leaving group, as well as displacement reactions where the leaving group on the pyridine ring is halogen, such as the Buchwald–Hartwig amination reaction. C–N bond forming nucleophilic reactions with cyano and alkoxy leaving groups on the pyridine ring are also discussed. Reactions requiring metal catalysts and those that proceed in the absence of any catalyst are reviewed. Metallation reactions on halopyridines, often used to introduce functionality into the pyridine ring, are included. Functional group transformations including rearrangement reactions leading to C–N bond formation such as Hofmann and Curtius rearrangement on pyridine derivatives are also reviewed.

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