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2005
Triazine derivatives
R 0655
Chloromethyl-, Dichloromethyl-, and Trichloromethyl-1,2,4-triazines and Their
Method for the Synthesis and tele-Substitution Reactions with
09- 167 4-Oxides:
C-Nucleophiles. — A simple procedure for the synthesis of 1,2,4-triazines (III) and
their 4-oxides (IV) containing a -CH2Cl, -CHCl2, or -CCl3 group at position 3 by
cyclization of α-oximinoacetophenone hydrazone (I) with the chloroacetonitriles (II)
is described. The reaction pathway depends on the number of halogen atoms in the corresponding acetonitrile. The reactions of 3-trichloromethyl-1,2,4-triazine (IIIc) with
aromatic C-nucleophiles (V) like indole or phenols are accompanied by tele-substitution with elimination of halogen to yield the 5-aryl substituted triazines (VI). —
(KOZHEVNIKOV*, D. N.; KATAEVA, N. N.; RUSINOV, V. L.; CHUPAKHIN, O.
N.; Russ. Chem. Bull. 53 (2004) 6, 1295-1300; Urals State Tech. Univ.,
Ekaterinburg 620002, Russia; Eng.) — H. Haber
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