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.
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References
J. Slouka and V. Bekarek, Coll. Czech. Chem. Commun., 1980, 45, 1379.
M. Busch, Ber., 1899, 32, 2959.
P. Pierron, Ann. Chim. (Paris), 1908, 15, 213.
P. Pierron, Ann. Chim. (Paris), 1908, 15, 252.
J. Slouka, Pharmazie, 1988, 43, 864.
L. Ergener, Rev. Faculte Sci. Univ. Istambul, 1950, 15A, 91.
D. L. Lipilin, O. Yu. Smirnov, A. M. Churakov, Yu. A. Strelenko, A. Yu. Tyurin, S. L. Ioffe, and V. A. Tartakovsky, Eur. J. Org. Chem., 2004, 4794.
D. L. Lipilin, P. A. Belyakov, Yu. A. Strelenko, A. M. Churakov, O. Yu. Smirnov, S. L. Ioffe, and V. A. Tartakovsky, Eur. J. Org. Chem., 2002, 3821.
H. Zollinger, DiazoChemistry I: Aromatic and Heteroaromatic Compounds, VCH, Weinheim, 1994.
M. M. M. Sallam, Y. A. Ibrahim, and S. A.-L. Abdel-Hady, Helv. Chim. Acta, 1976, 59, 1093.
A. Mustafa, W. Asker, A. K. Mansouz, H. A. A. Zaher, and A. R. Eloui, J. Org. Chem., 1963, 28, 3519.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 346–349, February, 2006.
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Lipilin, D.L., Churakov, A.M., Strelenko, Y.A. et al. Synthesis of 2-alkyl-1,2,4-benzotriazin-3(2h)-ones and 2-alkyl-1,4-dihydro-1,2,4-benzotriazin-3(2h)-ones. Russ Chem Bull 55, 357–361 (2006). https://doi.org/10.1007/s11172-006-0260-9
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DOI: https://doi.org/10.1007/s11172-006-0260-9