Synthesis and structural study of 2, 5-dihydropyridines. Competitive metalation of 2-fluoropyridine

F Marsais, P Granger, G Queguiner

Index: Marsais, F.; Granger, P.; Queguiner, G. Journal of Organic Chemistry, 1981 , vol. 46, # 22 p. 4494 - 4497

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Citation Number: 37

Abstract

Butyllithium addition to 2-fluoropyridine occurs at low temperature. Hydrolysis of the resulting reaction mixture leads to an adduct, the structure of which is shown to be 2-butyl-6- fluoro-2, 5-dihydropyridine. This result was chemically proved and conformed by'H and 13C NMR spectroscopy (we establish, moreover, some physicochemical properties of this structure, IR, UV, etc.). The 2-fluoropyridine-butyllithium adduct reacts with various alkyl ...