Amination of Phosphorodiamidate-Substituted Pyridines and Related N-Heterocycles with Magnesium Amides

Balkenhohl, Moritz; Heinz, Benjamin; Abegg, Thomas und Knochel, Paul (2018): Amination of Phosphorodiamidate-Substituted Pyridines and Related N-Heterocycles with Magnesium Amides. In: Organic Letters, Bd. 20, Nr. 24: S. 8057-8060

Abstract

The amination of various phosphorodiamidate-substituted pyridines, quinolines, and quinoxaline with magnesium amides R2NMgCl center dot LiCl proceeds at room temperature within 8 h. Several pharmaceutically active amines were suitable substrates for this amination procedure, and also the antihistaminic tripelennamine was prepared. Additionally, several heterocyclic phosphorodiamidates underwent directed ortho-metalation (DoM) using TMPMgCl center dot LiCl (TMP = 2,2,6,6-tetramethylpiperidyl) or TMP2Mg center dot 2LiCl, followed by electrophilic functionalization prior to the amination step, which led to ortho-functionalized aminated N-heterocycles.

• Dokumententyp: Zeitschriftenartikel
• Fakultät: Chemie und Pharmazie > Department Chemie
• Themengebiete: 500 Naturwissenschaften und Mathematik > 540 Chemie
• ISSN: 1523-7060
• Sprache: Englisch