Chemistry of heterocyclic compounds. 25. Selective metalation of the pyridine nucleus at the 3 position

GR Newkome, JD Sauer, SK Staires

Index: Newkome,G.R. et al. Journal of Organic Chemistry, 1977 , vol. 42, # 22 p. 3524 - 3527

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Citation Number: 10

Abstract

Treatment of bis (6-bromo-2-pyridyl) ketone ketal (3) with n-butyllithium in diethyl ether at- 40" C resulted in the isolation of pyridone 6 after normal hydrolytic workup. Selective metalation of the 3 position of 3 has been demonstrated by labeling studies. The formation of pyridone 6 is proposed to occur by first 1, 4-elimination-fragmenta-tion of one pyridine nucleus, followed by cyclization upon workup.