Chemical Communications

Unprecedented C-6 functionalisation of 3-picoline induced by a methyl to C-6 lithium shift

J Mathieu, P Gros, Y Fort

Index: Mathieu, Julien; Gros, Philippe; Fort, Yves Chemical Communications, 2000 , # 11 p. 951 - 952

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Citation Number: 21

Abstract

The selective lithiation-functionalisation of 3-picoline 1 remains a synthetic challenge since the potential electrophilicity of the azomethine bond towards alkyllithium reagents as well as a competitivity between acidic protons of the methyl group and those of the heteroaromatic ring must be considered. In fact, a survey of the literature revealed that major studies concern the abstraction of side-chain protons 1 while the selective lithiation of the pyridinic ring has been ...