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Regio- and chemi-selective, directed ortho-lithiation of 2-, 2,5- or 3,4-substituted pyridine N-oxides has been achieved with diisopropylamide and butyllithium. Polysubstituted pyridine N-oxides, azaxanthone, and an isomer of orelline have been synthesized by such methods.
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Mongin et al. (1995) studied this question.
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