Regioselectivity in the amination of azines: Reaction of pyrazine derivatives with O-mesitylenesulfonylhydroxylamine
Russian Journal of Organic Chemistry, ISSN: 1070-4280, Vol: 47, Issue: 6, Page: 889-896
2011
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Article Description
Treatment of 2-X-substituted pyrazines [X = H, Me, Et, Pr, i-Pr, t-Bu, MeCH(OH), HN, 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), HN, 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 σ, σ, and E , 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.
Bibliographic Details
http://www.scopus.com/inward/record.url?partnerID=HzOxMe3b&scp=80051501253&origin=inward; http://dx.doi.org/10.1134/s1070428011060108; http://link.springer.com/10.1134/S1070428011060108; http://link.springer.com/content/pdf/10.1134/S1070428011060108; http://link.springer.com/content/pdf/10.1134/S1070428011060108.pdf; http://link.springer.com/article/10.1134/S1070428011060108/fulltext.html; http://www.springerlink.com/index/pdf/10.1134/S1070428011060108; http://www.springerlink.com/index/10.1134/S1070428011060108; https://dx.doi.org/10.1134/s1070428011060108; https://link.springer.com/article/10.1134/S1070428011060108
Pleiades Publishing Ltd
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