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Synthesis of 2-alkyl-1,2,4-benzotriazin-3(2h)-ones and 2-alkyl-1,4-dihydro-1,2,4-benzotriazin-3(2h)-ones
Authors:D L Lipilin  A M Churakov  Yu A Strelenko  V A Tartakovsky
Institution:(1) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation
Abstract:A preparative method for the synthesis of 2-alkyl-1,2,4-benzotriazin-3(2H)-ones 3 was developed. The method involves treatment with sodium cyanate of 2-alkylbenzotetrazinium tetrafluoroborates, which exist in solutions in equilibrium with o-(alkylazo)aryldiazonium tetrafluoroborates. Reduction of compounds 3 with zinc in acetic acid afforded 2-alkyl-1,4-dihydro-1,2,4-benzotriazin-3(2H)-ones. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 346–349, February, 2006.
Keywords:diazonium salts  sodium cyanate  azo compounds  nitrogen-containing heterocycles  1  2  4-benzotriazin-3-ones  nucleophilic substitution  reduction            13C NMR spectroscopy  synthetic methods
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