Home Chemistry Heterocyclic Building Blocks Naphthyridines 1,7-Naphthyridine
Aromatic Substitution Reactions: Like other aromatic compounds, 1,7-naphthyridine can undergo electrophilic aromatic substitution reactions, where an electrophile replaces a hydrogen atom on the aromatic ring. Common electrophilic aromatic substitutions include nitration, halogenation, sulfonation, and Friedel-Crafts acylation/alkylation.
Reduction Reactions: 1,7-Naphthyridine can be reduced to the corresponding dihydronaphthyridine using reducing agents like lithium aluminum hydride (LiAlH4). The dihydronaphthyridine can then be further reduced to tetrahydronaphthyridine.
Oxidation Reactions: It can be oxidized to form various oxidation products, depending on the reagent used. For example, oxidation with chromic acid or potassium permanganate may lead to the formation of carboxylic acids or other functional groups, depending on reaction conditions.
Alkylation and Acylation: Like pyridine, 1,7-naphthyridine can undergo alkylation and acylation reactions at the nitrogen atom. These reactions are typically carried out in the presence of strong bases to generate the corresponding N-alkyl or N-acyl derivatives.
Condensation Reactions: 1,7-Naphthyridine can participate in condensation reactions with other compounds, forming various heterocyclic compounds. For example, it can react with aldehydes and ketones in the presence of acidic or basic catalysts to form 1,7-naphthyridine derivatives.
Metalation Reactions: The nitrogen atom in 1,7-naphthyridine can coordinate with various metal ions, forming metal complexes. These complexes can be used in catalytic or coordination chemistry.
Nucleophilic Substitution Reactions: While not as common as electrophilic aromatic substitutions, nucleophilic substitution reactions can occur at certain positions of 1,7-naphthyridine under appropriate conditions. This may involve the displacement of leaving groups by nucleophiles.
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tert-Butyl (8-chloro-1,7-naphthyridin-3-yl)carbamate
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5-Bromo-1,7-naphthyridine-3-carboxylic acid
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