Chemistry Heterocyclic Building Blocks Pyridines 2-bromo-3-nitropyridine
Ambeed provide 5 derivatives of 2-bromo-3-nitropyridine.
These compounds have the same murcko framework: 2-bromo-3-nitropyridineSubstitution Reactions: The bromine atom in the 2-position of the pyridine ring can undergo substitution reactions with various nucleophiles, such as amines or thiols, to replace the bromine atom with the nucleophile. For example, nucleophilic substitution with primary amines can lead to the formation of 2-aminopyridine derivatives.
Reduction Reactions: The nitro group present at the 3-position can be reduced to an amino group using reducing agents like iron and hydrochloric acid, tin and hydrochloric acid, or other metal hydrides like palladium on carbon (Pd/C) under hydrogen atmosphere. This reduction yields 2-bromo-3-aminopyridine derivatives.
Cross-Coupling Reactions: The bromine atom can participate in cross-coupling reactions, such as Suzuki coupling or Heck reaction, with appropriate partners. This allows for the synthesis of more complex molecules by coupling with aryl or vinyl halides.
Nucleophilic Aromatic Substitution (SNAr): The nitro group can undergo nucleophilic aromatic substitution under basic conditions, leading to the formation of 2-bromo-3-nitroaryl derivatives.
Metalation Reactions: The pyridine ring can be deprotonated using strong bases like n-butyllithium (n-BuLi) or sodium amide (NaNH2), followed by reaction with electrophiles, allowing for the introduction of various functional groups.
Functional Group Interconversion: The bromo and nitro groups can serve as handles for further functionalization reactions, such as halogenation, reduction, oxidation, or conversion to other functional groups through appropriate chemical manipulations.
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