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Paper | Special issue | Vol 86, No. 1, 2012, pp. 391 - 410
Published online: 27th July, 2012
DOI: 10.3987/COM-12-S(N)33
■ Side-Chain Lithiation of 2- and 4-Substituted Pyridines: Synthesis of More Complex Substituted Pyridines

Keith Smith,* Gamal A. El-Hiti,* Ahmed Fekri, and Mohammed B. Alshammari

*School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, CF10 3AT, U.K.

Abstract

Lithiation of pyridines substituted in the 2- and 4-positions by acylaminomethyl groups, namely of the corresponding N-(pyridinylmethyl)pivalamides, N' -(pyridinylmethyl)-N,N-dimethylureas and tert-butyl N-pyridinylmethylcarbamates, with two mole equivalents of t BuLi in anhydrous THF at 78 °C takes place on the nitrogen and on the methylene group of the side-chain. The lithium reagents thus obtained react with a variety of electrophiles to give the corresponding side-chain substituted derivatives in high yields.

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