Abstract: 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 sigma(I), sigma (R) (o) , and E (s) (o) , on the other. The obtained data on the regioselectivity of amination of pyrazines were interpreted in terms of DFT/PBE/3Z quantum-chemical calculations.

Cite: Borodkin G.I. , Vorob'ev A.Y. , Shakirov M.M. , Shubin V.G.
Regioselectivity in the amination of azines: Reaction of pyrazine derivatives with O-mesitylenesulfonylhydroxylamine
Russian Journal of Organic Chemistry. 2011. V.47. N6. P.889-896. DOI: 10.1134/S1070428011060108 WOS Scopus РИНЦ

ArticleLinkType.TRANSLATED_TO_ORIGINAL: Бородкин Г.И. , Воробьев А.Ю. , Шакиров М.М. , Шубин В.Г.
О региоселективности аминирования азинов: взаимодействие производных пиразина с о-мезитиленсульфонилгидроксиламином
Журнал органической химии (RUSS J ORG CHEM+). 2011. Т.47. №6. С.19-20. РИНЦ

Dates:

Published print:	Jun 1, 2011
Published online:	Jul 8, 2011

Identifiers:

Web of science	WOS:000292562900010
Scopus	2-s2.0-80051501253
Elibrary	18058337
OpenAlex	W1975642448

Altmetrics: