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Synlett 1991; 1991(5): 347-348
DOI: 10.1055/s-1991-34743
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Efficient Alkylation of Nitrogen Heterocycles Using Lithium Salts and Oxygen Leaving Groups

Gary A. Epling* , Anil Kumar
  • *Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269, USA
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Publication Date:
07 March 2002 (online)

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Superior yields of N-alkylated nitrogen heterocycles have been achieved with remarkable regioselectivity. The lithium salt of the heterocycle was prepared by treatment with butyllithium in tetrahydrofuran. Reaction of this salt at room temperature with electrophiles, such as alkyl methanesulfonates and 1,2-epoxypropane, bearing an oxygen leaving group proceeded quantitatively and gave exclusive N-alkylation with no detectable C-alkylation.