The Journal of Organic Chemistry

Lithiation of methoxypyridines directed by. alpha.-amino alkoxides

DL Comins, MO Killpack

Index: Comins, Daniel L.; Killpack, Michael O. Journal of Organic Chemistry, 1990 , vol. 55, # 1 p. 69 - 73

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Citation Number: 97

Abstract

The addition of methoxypyridinecarboxaldehydes to certain lithium dialkylamides gave a- amino alkoxides in situ that were ring-lithiated with alkyllithium bases. Alkylation and hydrolysis on workup provided ringsubstituted methoxypyridinecarboxaldehydes via a one- pot reaction. The one-pot methylation of isomeric methoxypyridinecarboxaldehydes was examined. The regioselectivity of the lithiation-methylation was dependent on the ...