Zn‐, Mg‐, and Li‐TMP Bases for the Successive Regioselective Metalations of the 1,5‐Naphthyridine Scaffold (TMP=2,2,6,6‐Tetramethylpiperidyl)

Abstract

Abstract 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 3 ⋅OEt 2 ) 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.