The methylation of N-cyano N-methyl hydrazones: A new access to 2-aminoimidazoles through an in situ 1,3,4-triaza cope rearrangement
(1997) Societes Chimiques Belges. Bulletin — Vol. 106, n° 9-10, p. 553-557 (1997)
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- Abstract
- The reaction of 1-methyl-1-cyanohydrazones with methyl trifluoromethane sulfonate allows the direct preparation of 2-(methylamino)-1-methyl imidazoles as their triflic acid salts. The reaction pathway is believed to involve the formation of the 1-cyano-1,2-dimethyl ene-hydrazine derivative, which then undergoes a [3,3] rearrangement at room temperature, followed by an in situ cyclisation. None of the intermediates could be isolated or observed by H-1 NMR. Thus, the 2-(methylamino)-1-methyl imidazoles are obtained in good to average yields In two steps from the corresponding ketones and 1-methyl-1-cyanohydrazine.
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Ryckmans, T., Schulte, K., & Viehe, HG. (1997). The methylation of N-cyano N-methyl hydrazones: A new access to 2-aminoimidazoles through an in situ 1,3,4-triaza cope rearrangement. Societes Chimiques Belges. Bulletin, 106(9-10), 553-557. https://hdl.handle.net/2078.5/87996 (Original work published 1997)