The amination of various phosphorodiamidate-substituted pyridines, quinolines, and quinoxaline with magnesium amides RNMgCl·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 (D oM) using TMPMgCl·LiCl (TMP = 2,2,6,6-tetramethylpiperidyl) or TMPMg·2LiCl, followed by electrophilic functionalization prior to the amination step, which led to ortho-functionalized aminated N-heterocycles.
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Amination of Phosphorodiamidate-Substituted Pyridines and Related N-Heterocycles with Magnesium Amides.
Org Lett
December 2018
Department of Chemistry , Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, Haus F , 81377 Munich , Germany.
The amination of various phosphorodiamidate-substituted pyridines, quinolines, and quinoxaline with magnesium amides RNMgCl·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 (D oM) using TMPMgCl·LiCl (TMP = 2,2,6,6-tetramethylpiperidyl) or TMPMg·2LiCl, followed by electrophilic functionalization prior to the amination step, which led to ortho-functionalized aminated N-heterocycles.
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