Reactions of 3-R-5-nitropyridines with nucleophiles: Nucleophilic substitution vs conjugate addition
2019
Bastrakov, Maxim A. | Nikol’skiy, Vladislav V. | Starosotnikov, Alexey M. | Fedyanin, Ivan V. | Shevelev, Svyatoslav A. | Knyazev, Daniil A.
A number of 3-R-5-nitropyridines were synthesized and their reactions with various types of nucleophiles were investigated. The reaction outcome depends on the nature of a nucleophile: in case of anionic O-, N- and S-nucleophiles the previously unreported substitution of non-activated nitro group occurred while carbon nucleophiles underwent dearomatization of the pyridine ring with the formation of products of 1,2- and 1,4-addition.
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