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At the beginning of the seventies he was interested in the synthesis of orthohalolithiopyridines from the corresponding bromopyridines as precursors of 2,3- and 3,4- pyridynes, with the aim of reacting them with dienes to form quinolines. Two side reactions were observed, the first one a proton abstraction ortho to the bromine and the second one involving bromine migration. These discoveries allowed the development of two new strategies in the azaheteroaromatic series, the directed ortho-lithiation and the halogen dance reactions, as well as their further application to electrophilic-like substitution of π-deficient heterocycles.
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ChemInformno. 3 (2010)
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