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New synthetic approaches to fluorinated 3-phenyl-1,2,4-benzotriazines for biological testing have been elaborated. 1-(3,4-Difluorophenyl)-3,5-diphenylformazan (IVa) was synthesized via dinitriding of 3,4-difluoroaniline, followed by azo-addition of the resulting azobenzenediazonium chloride with acetaldehyde phenylhydrazone. 6,7-Difluoro-3-phenyl-1,2,4-benzotriazine (Va) was obtained via intramolecular cyclization of formazan IVa in the presence of BF3/AcOH complex. Monofluoro-substituted 6-R-7-fluoro-3-phenyl-1,2,4-benzotriazine derivatives (Vb -Vq) were prepared by substituting fluorine atom with alkoxides in 3,4-difluoronitrobenzene. Conditions for nucleophilic substitution of the second fluorine atom in benzotriazines V have been established. Fluorinated 3-phenyl-1,2,4-benzotriazines have been tested for antiviral and cytotoxic activity on Vero cell cultures and proved to be active against severe diseases caused by smallpox and some other pathogenic viruses.

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The reactions of 3 fluoro 4 R 6 phenylsulfonylmethylnitrobenzenes with dimethyl fumarate or diethyl maleate in acetonitrile in the presence of an excess of K 2 CO 3 and a catalytic amount of 18 crown 6 afforded mixtures of dialkyl 6 R 7 fluoro and dialkyl 6 R 7 phenylsulfonylquinoline 2,3 carboxylate N oxides, as well as dialkyl 6 R 7 fluoro quinoline 2,3 carboxylates (alkyl is methyl or ethyl), which were resolved by column chromatography and identified by 1 H NMR spectroscopy and X ray diffraction.Key words: vicarious nucleophilic substitution of hydrogen, 4 R 3 fluoronitrobenzenes, 3 fluoro 4 R 6 phenylsulfonylmethylnitrobenzenes, dimethyl fumarate, diethyl maleate, dimethyl 6 R 7 fluoroquinoline 2,3 carboxylate N oxides, diethyl 6 R 7 fluoroquinoline 2,3 carboxylate N oxides, dimethyl 6 R 7 phenylsulfonylquinoline 2,3 carboxylate N oxides, diethyl 6 R 7 phenylsulfonylquinoline 2,3 carboxylate N oxides, dimethyl 6 R 7 fluoro quinoline 2,3 carboxylates, diethyl 6 R 7 fluoroquinoline 2,3 carboxylates.