Abstract: Cyclization reactions of nitro-substituted electrophilic building blocks with various nucleophiles allow for the synthesis of various nitro-substituted carbo- and heterocycles. The electron-withdrawing nitro group can be easily transformed to an electron-donating amino group which is not only pharmacologically relevant, but can also act as a nucleophile in inter- and intramolecular reactions with electrophiles, such as aldehydes, and can also be converted to other functional groups. The nitro group has the capacity to activate compounds for regioselective palladium catalyzed CH-arylation reactions. Inter- and intramolecular CH-arylations of nitro-substituted heterocyclic building blocks, such as 4-nitropyrazoles, 4-nitroimidazoles, 2-nitroindole and nitro-substituted purine analogues, allow for a convenient diversity-oriented approach to the corresponding arylated products. In addition, the nitro group can act as a leaving group in S_NAr reactions.

Review: Synlett 2024, DOI: 10.1055/s-00000083.

Period of investigation: 2007 - 2019

Keywords: nitro compounds; cyclizations; heterocycles; silyl enol ethers; heterocyclic enamines