Zn-, Mg-, and Li-TMP Bases for the Successive Regioselective Metalations of the 1,5-Naphthyridine Scaffold (TMP=2,2,6,6-Tetramethylpiperidyl),Chemistry - A European Journal

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Zn-, Mg-, and Li-TMP Bases for the Successive Regioselective Metalations of the 1,5-Naphthyridine Scaffold (TMP=2,2,6,6-Tetramethylpiperidyl)
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2017-08-23 12:20:57 , DOI: 10.1002/chem.201703638
Moritz Balkenhohl ₁ , Robert Greiner ₁ , Ilya S. Makarov ₁ , Benjamin Heinz ₁ , Konstantin Karaghiosoff ₁ , Hendrik Zipse ₁ , Paul Knochel ₁

Affiliation

Step by step: Successive regioselective metalations of the 1,5-naphthyridine scaffold are achieved by using a combination of Zn-, Mg-, and Li-TMP (TMP=2,2,6,6-tetramethylpiperidyl) bases in the presence or absence of BF₃⋅OEt₂ allowing the introduction of up to three substituents. A novel “halogen dance” rearrangement allows the introduction of a fourth substituent leading to 2,4,7,8-tetrafunctionalized 1,5-naphthyridines. Also, two key 1,5-naphthyridines for the synthesis of OLED materials and an antibacterial agent were prepared.

中文翻译：

Zn，Mg和Li-TMP碱用于1,5-萘啶支架的连续区域选择性金属化（TMP = 2,2,6,6-四甲基哌啶基）

逐步操作：在存在或不存在Zn-，Mg-和Li-TMP（TMP = 2,2,6,6-四甲基哌啶基）的基础上，实现1,5-萘吡啶骨架的连续区域选择性金属化BF _3· OEt _2的不存在，最多可引入三个取代基。新颖的“卤素舞”重排允许引入导致2,4,7,8-四官能化的1,5-萘啶的第四取代基。另外，制备了用于合成OLED材料的两个关键的1，5-萘啶和抗菌剂。

更新日期：2017-08-24

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