Description:
<jats:title>Abstract</jats:title><jats:p>A set of successive regioselective metalations and functionalizations of the 1,5‐naphthyridine scaffold are described. A combination of Zn‐, Mg‐, and Li‐TMP (TMP=2,2,6,6‐tetramethylpiperidyl) bases and the presence or absence of a Lewis acid (BF<jats:sub>3</jats:sub>⋅OEt<jats:sub>2</jats:sub>) allows the introduction of up to three substituents to the 1,5‐naphthyridine core. Also, a novel “halogen dance” reaction was discovered upon metalation of an 8‐iodo‐2,4‐trifunctionalized 1,5‐naphthyridine allowing a fourth regioselective functionalization. Additionally, reactions leading to key 1,5‐naphthyridines for the preparation of OLED materials and a potential antibacterial agent were performed.</jats:p>