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■ Synthesis of the First Monosubstituted 1,2,4-Triazine Di-N-oxide. ¹³C NMR of 1,2,4-Triazine N-Oxides and Use of Hydrogen/Deuterium Isotope Shifts for the Assignments of Some Dihydro-1,2,4-triazine Tautomers

Misa V. Jovanovic*

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

Abstract

3-Amino-1,2,4-triazine 2,4-dioxide (4) was prepared by oxidation of 3-amino-1,2,4-triazine 2-oxide (3) with hydrogen peroxide in polyphosphoric acid, the first 1,2,4-triazine 2,4-dioxide ever reported. Same starting material gave ring contracted products as well as ring C-oxidation under a variety of reaction conditions employed in the attempted synthesis of the title compound (4). ¹³C nmr proved to be a method of choice for structural assignments of isomeric N-oxides. H/D isotope shifts unequivocally established the structures of compounds which could conceivably exist as several tautomers.