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- Title
Regioselectivity in the amination of azines: Reaction of pyrazine derivatives with O-mesitylenesulfonylhydroxylamine.
- Authors
Borodkin, G. I.; Vorob'ev, A. Yu.; Shakirov, M. M.; Shubin, V. G.
- Abstract
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.
- Subjects
PYRAZINES; AMINATION; STATISTICAL correlation; RESONANCE; STERIC hindrance
- Publication
Russian Journal of Organic Chemistry, 2011, Vol 47, Issue 6, p889
- ISSN
1070-4280
- Publication type
Article
- DOI
10.1134/S1070428011060108