845823-92-9Relevant academic research and scientific papers
Chloromethyl-, dichloromethyl-, and trichloromethyl-1,2,4-triazines and their 4-oxides: Method for the synthesis and tele-substitution reactions with C-nucleophiles
Kozhevnikov,Kataeva,Rusinov,Chupakhin
, p. 1295 - 1300 (2007/10/03)
A simple procedure was developed for the synthesis of 1,2,4-triazines and their 4-oxides containing the ClCH2, Cl2CH, or CCl 3 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.
