benzopyridines

Benzopyridines are a class of heterocyclic compounds in which a benzene ring is fused to a pyridine ring, creating a bicyclic aromatic system. The best-known representatives are quinoline and isoquinoline, which differ in the fusion pattern of the rings. In these molecules, the pyridine nitrogen remains part of the fused framework, giving a nitrogen atom that is basic like pyridine and participates in the compounds’ chemistry.

Quinoline and isoquinoline are colorless solids or liquids with high aromaticity and planarity. The nitrogen atom in the ring system influences reactivity, basicity, and coordination behavior, and substitutions on the rings can tune electronic properties and solubility. As scaffolds, benzopyridines support a wide range of derivatives used in research and industry.

Benzopyridines occur naturally in various alkaloids and are widely used as synthetic intermediates and pharmacophores. Quinoline derivatives are prominent in medicinal chemistry, including antimalarials and antimicrobial agents; quinoline alkaloids such as quinine have historical significance in medicine. Isoquinoline derivatives also appear in numerous pharmacologically active compounds, including benzylisoquinoline alkaloids and various therapeutic agents. Beyond pharmaceuticals, benzopyridines serve as dyes, ligands for metal complexes, and fluorescent probes in analytical applications.

Synthesis of benzopyridines relies on cyclization and condensation routes that build the fused ring system from suitable precursors. Classic methods include heterocyclization of anilines with carbonyl compounds and related reagents, yielding quinoline or isoquinoline frameworks with variable substitution. The methods accommodate diverse substituents, enabling exploration of structure–activity relationships in research and development.