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KMID : 1059519890330040419
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Journal of the Korean Chemical Society
1989 Volume.33 No. 4 p.419 ~ p.425
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1,2,4-Triazine III : Synthesis of 1-Methyl-1,2,4-triazinium Iodides and Their Ring Contraction Reaction to 1-Methyl-1,2,4-triazoles
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Lee Jae-Keun
Ryu Hyang-Sun
Paudle W. W.
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Abstract
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Various 1-methyl-1,2,4-triazinium iodides were easily synthesized by the reaction of various 1,2,4-triazines and methyl iodide in acetone. When methyl iodide salts of 1,2,4-triazine derivatives were treated with K3Fd(CN)6 in 10% NaOH solution, 1-methyl-1,2,4-triazole derivatives as the main products were obtained by ring contraction. In addition to 1-methyl-1,2,4-triazole derivatives, 1,6-dihydro-6-oxo-1,2,4-triazine derivatives as the minor products were also obtained when there were no substitutents in C6-position of 1,2,4-triazines. The formation of pseudo base by OH- and then oxidation to either 1,6-dihydro-6-oxo-1,2,4-triazines or 1-methyl-1,2,4-triazoles were suggested as the mechanism of the ring contraction. This mechanism also verified that the position of quaternization was neither N2 nor N4 but 1-nitrogen of 1,2,4-triazine.
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