Deprotonation of pyridine carboxamides using lithium magnesiates bases

H Hawad, O Bayh, C Hoarau, F Trécourt, G Quéguiner…

Index: Hawad, Hacan; Bayh, Omar; Hoarau, Christophe; Trecourt, Francois; Queguiner, Guy; Marsais, Francis Tetrahedron, 2008 , vol. 64, # 14 p. 3236 - 3245

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Citation Number: 17

Abstract

Regioselective deprotonation of N-methyl-and tert-butylpyridine carboxamides using lithium magnesiates bases was achieved at room temperature avoiding nucleophilic addition on the pyridine molecule and auto-condensation of the arylmetal intermediates on the amide group was described. The hydrogen–magnesium exchange was evidenced using 1H NMR spectroscopy at room temperature and the reactivity of the lithium 2-, 3-and 4- ...