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Communication | Regular issue | Vol 19, No. 10, 1982, pp.1865-1868
Published online, 1st January, 1970
DOI: 10.3987/R-1982-10-1865
Studies on as-Triazine Derivatives. II. A Ring-cleavage Reaction of 3-Trichloromethyl-5,6-diphenyl-1,2,4-triazine and Related Compounds

Shoetsu Konno, Masaaki Yokoyama, and Hiroshi Yamanaka

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan

Abstract

3-Chloromethyl- (4), 3-dichloromethyl- (3), and 3- trichloromethyl-5,6-diphenyl-1,2,4-triazine (2) were synthesized from 3-methyl-5,6-diphenyl-1,2,4-triazine (1). The reaction of 4 with sodium ethoxide in ethanol simply afforded the corresponding 3-ethoxymethyl compound. In contrast to this reaction, when 2 and 3 were treated with sodium alkoxide, an unexpected ring-cleavage reaction occurred instead of simple nucleophilic attack to chloromethyl groups. The structure of the products and the reaction mechanism are discussed.