Improved Synthesis of C~ 2-Symmetrical Pyridinediols and Synthesis of C~ s-Symmetrical Pyridinediols

B Koning, J Buter, R Hulst, R Stroetinga…

Index: Koning, Bartjan; Buter, Jan; Hulst, Ron; Stroetinga, Roelof; Kellogg, Richard M. European Journal of Organic Chemistry, 2000 , # 15 p. 2735 - 2743

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Citation Number: 20

Abstract

Base-induced reaction of 2, 6-dimethylpyridine (2, 6-lutidine)(1) with two equivalents of various ketones has been reported to provide C2-symmetrical pyridine diols 3. Closer examination reveals that competitive di-addition to a single methyl group can occur providing Cs-symmetrical pyridine diols 7. By varying the lithiation times, the formation of this side product could be maximized or minimized on the basis