1201762-98-2Relevant academic research and scientific papers
Regioselectivity in the amination of azines: Reaction of pyrazine derivatives with O-mesitylenesulfonylhydroxylamine
Borodkin,Vorob'ev,Shakirov,Shubin
experimental part, p. 889 - 896 (2011/10/02)
Treatment of 2-X-substituted pyrazines [X = H, Me, Et, Pr, i-Pr, t-Bu, MeCH(OH), H2N, AcNH] with O-mesitylenesulfonylhydroxylamine gave the corresponding 2-X- and 3-X-(1-amino)pyrazin-1-ium mesitylenesulfonates. 2-Alkylpyrazines (X = Me, Et, Pr, i-Pr) displayed a correlation between the logarithms of the concentration ratio of 2- and 3-substituted cations and substituent steric constants. Wider series of substituted pyrazines [X = H, Me, Et, Pr, i-Pr, MeCH(OH), H2N, AcNH] conformed to a multiparameter correlation between the logarithms of the concentration ratio of 2- and 3-substituted cations, on the one hand, and substituent constants σI, σR?, and E s?, on the other. The obtained data on the regioselectivity of amination of pyrazines were interpreted in terms of DFT/PBE/3Z quantum-chemical calculations. Pleiades Publishing, Ltd., 2011.
Regioselectivity in 2-X-pyrazine aminations by O-mesitylenesulfonylhydroxylamine
Borodkin, Gennady I.,Vorob'ev, Aleksey Yu.,Shakirov, Makhmut M.,Shubin, Vyacheslav G.
supporting information; experimental part, p. 6779 - 6782 (2010/04/29)
The regioselectivity of 2-X-pyrazine aminations by O-mesitylenesulfonylhydroxylamine was studied experimentally and the results are discussed from the viewpoint of electronic and steric factors. DFT calculations are consistent with the reaction proceeding according to an SN2 mechanism.
