Chloromethyl-, dichloromethyl-, and trichloromethyl-1,2,4-triazines and their 4-oxides: method for the synthesis and tele-substitution reactions with C-nucleophiles |
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Authors: | Kozhevnikov D. N. Kataeva N. N. Rusinov V. L. Chupakhin O. N. |
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Affiliation: | (1) Urals State Technical University, 19 ul. Mira, 620002 Ekaterinburg, Russian Federation, Russia |
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Abstract: | A simple procedure was developed for the synthesis of 1,2,4-triazines and their 4-oxides containing the ClCH2, Cl2CH, or CCl3 group at position 3 by cyclization of 2-aryl-2-hydrazono-1-oximinoethanes with the corresponding chloroacetonitriles. The reaction pathway depends on the number of halogen atoms in the acetonitrile used. The reactions with trichloroacetonitrile, monochloroacetonitrile, and dichloroacetonitrile afford 3-trichloromethyl-1,2,4-triazines, 3-chloromethyl-1,2,4-triazine 4-oxides, and a mixture of the corresponding dichloromethyltriazines and their 4-oxides, respectively. The reactions of 3-trichloromethyl-1,2,4-triazines with indoles and phenols are accompanied by tele-substitution with elimination of halogen from the trichloromethyl group to give 5-indolyl- (or 5-hydroxyphenyl)-3-dichloromethyl-1,2,4-triazines. |
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Keywords: | tele-substitution of chlorine 3-trichloromethyl-1,2,4-triazines 3-chloromethyl-1,2,4-triazine 4-oxides indoles phenols |
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