Chemistry Heterocyclic Building Blocks Pyridines 3-chloro-5-nitropyridine
Substitution Reactions: The chlorine atom can undergo substitution reactions with various nucleophiles, such as amines or hydroxide ions, leading to the formation of substituted products.
Reduction: The nitro group (-NO2) can be reduced to an amino group (-NH2) under suitable conditions, such as using reducing agents like hydrogen gas in the presence of a catalyst, or using metal hydrides like sodium borohydride or iron with an acid. This reduction can lead to the formation of 3-chloro-5-aminopyridine.
Electrophilic Aromatic Substitution (EAS): The aromatic ring can undergo EAS reactions, where electrophiles attack the aromatic ring. For example, Friedel-Crafts acylation or Friedel-Crafts alkylation reactions can occur, leading to the introduction of acyl or alkyl groups onto the ring.
Nucleophilic Aromatic Substitution (SNAr): The nitro group can undergo nucleophilic aromatic substitution reactions, where the nitro group is replaced by a nucleophile. This reaction is facilitated under basic conditions.
Metalation: The pyridine ring can be metalated at the 2-position using strong bases like butyllithium or sodium amide, generating a reactive intermediate that can undergo further reactions, such as coupling reactions or subsequent functional group transformations.
Heterocyclic Chemistry: The presence of the pyridine ring makes it amenable to various heterocyclic chemistry reactions, such as condensation reactions to form fused heterocyclic systems or cyclization reactions with suitable reagents.
Cross-Coupling Reactions: The compound can undergo cross-coupling reactions, such as Suzuki-Miyaura, Heck, or Sonogashira reactions, especially if suitable functional groups are present for coupling partners.
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