Abstract
The reactions of 2-amino-4-methyl-5-(5-nitro-2-furyl)thiazole with excess methyl iodide leads to 3,4-dimethyl-2-methylamino-5-(5-nitro-2-furyl)thiazolium iodide, which is converted to 2-imino-3,4-dimethyl-5-(5-nitro-2-furyl)thiazoline under the influence of bases. The iminothiazoline structure was proved by comparison of the spectral characteristics of its acetyl derivative and the isomeric 2-(N-acetyl-N-methyl) amino-4-methyl-5-(5-nitro-2-furyl)thiazole. The pKa values of 2-amino-4-methyl-5-(5-nitro-2-furyl)thiazole and 3,4-dimethyl-2-imino-5-(5-nitro-2-furyl)-thiazoline were determined, and the constant of the aminothiazole-iminothiazoline tautomeric equilibrium was calculated.
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Translated from Khimiya Geterosiklicheskikh Soedinenii, No. 10, pp. 1337–1340, October, 1985.
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Usova, E.B., Krapivin, G.D. & Kul'nevich, V.G. Synthesis and properties of 5-(5-nitro-2-furyl)thiazolines. Chem Heterocycl Compd 21, 1094–1097 (1985). https://doi.org/10.1007/BF00515245
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DOI: https://doi.org/10.1007/BF00515245