Synthesis and ring-chain tautomerism of salts of alkylidene(arylidene) derivatives of amidrazones
A number of salts of alkylidene (arylidene) derivatives of amidrazones was obtained by the reaction of S-methylthioamidium iodides with hydrazones of monocarbonyl compounds. According to the 1H and 13C NMR data, these compounds in solutions are capable of ring-chain tautomerism of the 1-alkylideneamidrazone-1,2,4-triazoline type. The position of the equilibrium is determined chiefly by steric interactions of the substituents attached to the C-N2 bond.
KeywordsOrganic Chemistry Iodide Hydrazones Steric Interaction Monocarbonyl
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- 1.K. N. Zelenin, V. A. Khrustalev, V. P. Sergutina, and V. V. Pinson, Zh. Org. Khim., 17, 1825 (1981).Google Scholar
- 2.V. A. Khrustalev, K. N. Zelenin, V. P. Sergutina, and V. V. Pinson, Khim. Geterotsikl. Soedin., No. 8, 1138 (1980).Google Scholar
- 3.K. N. Zelenin, V. A. Khrustalev, V. V. Pinson, and V. V. Alekseev, Zh. Org. Khim., 16, 2237 (1980).Google Scholar
- 4.U. Masayuki and K. Seiju, J. Heterocycl. Chem., 15, 807 (1978).Google Scholar
- 5.H. Sildknecht and G. Hatzmann, Lieb. Ann., 724, 226 (1969).Google Scholar
- 6.M. Uda and S. Kubota, J. Heterocycl. Chem., 15, 1273 (1979).Google Scholar
- 7.K. N. Zelenin, V. A. Khrustalev, and V. P. Sergutina, Zh. Org. Khim., 16, 942 (1980).Google Scholar
- 8.I. L. Knunyants and L. V. Razvadovskaya, Zh. Obshch. Khim., 9, 557 (1939).Google Scholar
- 9.W. Walter, W. Ruback, and C. O. Meese, Chem. Ber., 113, 171 (1980).Google Scholar
- 10.T. Curtius and L. Pflug, J. Prakt. Chem., 44 , 535 (1981).Google Scholar
- 11.N. Kizhner, Zh. Russk. Fiz. Khim. Ova., Ch. Khim., 47, 1111 (1915).Google Scholar
- 12.G. J. Karabatsos and R. A. Taller, Tetrahedron, 24, 3557 (1978).Google Scholar