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

Balkenhohl, Moritz; Heinz, Benjamin; Abegg, Thomas; Knochel, Paul (2018): Amination of Phosphorodiamidate-Substituted Pyridines and Related N-Heterocycles with Magnesium Amides. In: Organic Letters, Vol. 20, No. 24: pp. 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.

• Item Type: Journal article
• Faculties: Chemistry and Pharmacy > Department of Chemistry
• Subjects: 500 Science > 540 Chemistry
• ISSN: 1523-7060
• Language: English