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Report | Regular issue | Vol 23, No. 9, 1985, pp.2299-2315
Published online, 1st January, 1970
DOI: 10.3987/R-1985-09-2299
Preparation and Structure Elucidation of Some N-Alkylpyrazinium Salts and Their N-Oxides

Misa V. Jovanovic*

*Department of Chemistry, Southern Methodist University, P.O. Box 750314, Dallas, TX 75275-0314, U.S.A.

Abstract

Several N4-alkylpyrazinium N-oxide salts were prepared in high yields by heating the corresponding pyrazine N1-oxides in the presence of alkylating reagent and solvent. The proton nmr data point to the quinoidal nature of these compounds. Pyrarine di-N-oxides deoxygenated rapidly under same reaction conditions to yield a mixture of N-alkylpyrazinium and N-alkylpyrazinium mono-N-oxide salts. Mechanism is proposed to account for these reductive deoxygenations of the pyrazine nucleus.