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Balkenhohl, Moritz; Greiner, Robert; Makarov, Ilya S.; Heinz, Benjamin; Karaghiosoff, Konstantin; Zipse, Hendrik; Knochel, Paul (2017): Zn-, Mg-, and Li-TMP Bases for the Successive Regioselective Metalations of the 1,5-Naphthyridine Scaffold (TMP=2,2,6,6-Tetramethylpiperidyl). In: Chemistry-A European Journal, Vol. 23, No. 53: pp. 13046-13050
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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 (BF3 center dot OEt2) 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.