AbstractThe intramolecular nucleophilic cyclization of 4‐(3‐pyridyl)butylamine (4a) to yield 6,7,8,9‐tetrahydro‐5H‐pyrido[2,3‐b]azepine (5) was investigated. Of eleven different alkali metal reagents sodium, sodium hydride, sodium amide, and potassium hydride gave good yields of5. The sodium conditions when applied to 3‐(3‐pyridyl)propylamine (4b) afforded 1,2,3,4‐tetrahydro‐1,8‐naphthyrid