Abstract
Enehydrazine derivatives have been obtained by the reaction of 6-phenyl-1,2,4-triazine 4-oxide with pyrazolones 2, which on further heating with pyrazolones 2 are converted into the corresponding symmetrical or unsymmetrical derivatives of dipyrazolylmethane. Enehydrazine derivatives of 1,3-dimethyl-5-nitrosouracil and 1,3-dimethylimidazolidine interact with 3-methyl-1-phenyl-5-pyrazolone (2a) with the formation of dipyrazolylmethane derivative. On interacting compound 2a or 3-methyl-1-(p-nitrophenyl)-5-pyrazolone with 3,6-diphenyl-1,2,4-triazine 4-oxide 12 the corresponding 4,4'-bispyrazolones are formed, but the interaction of compound 12 with 3-(p-nitrophenyl)-1-phenyl-5-pyrazolone leads to dipyrazolylmethane derivative. Dipyrazolylmethane derivative is obtained on heating of fervenulin 4-oxide, 2,4-dihydroxy-5-nitropyrimidine, and 1,3,5-triazines: 6-azauracil, 5-azauracil, azacytosine, and 2,4-diamino-s-triazine with pyrazolone 2a.
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REFERENCES
Yu. A. Azev,H. Neunhoeffer, andS. V. Shorshnev, Mendeleev Commun., 116 (1996).
V. L. Rusinov,D. N. Kozhevnikov,E. N. Ulomskii,O. N. Chupakhin,A. A. Aleksandrov, andH. Neunhoeffer, Zh. Org. Khim., 34, 429 (1998).
T. K. Sevast'yanova andL. B. Volodarskii, Khim. Geterotsikl. Soedin., 134 (1973).
Yu. A. Azev,H. Neunhoeffer,S. Foro,H. J. Lindner, andS. V. Shorshnev, Mendeleev Commun., 229 (1995).
V. A. Dokichev andA. A. Potekhin, Zh. Org. Khim., 13, 2617 (1977).
H. Gnichtel andB. Töpper, Liebigs Ann. Chem., 1071 (1989).
D. N. Kozhevnikov,V. N. Kozhevnikov,V. L. Rusinov,O. N. Chupakhin,E. O. Sidorov, andN. A. Klyuev, Zh. Org. Khim., 34, 423 (1998).
Yu. A. Azev,I. V. Teplyashina, andS. V. Shorshnev, Mendeleev Commun., 199 (1998).
Yu. A. Azev andG. G. Aleksandrov, Khim.-farm. Zh., No. 1, 49 (1997).
W. Hänsel, Liebigs Ann. Chem., 1680 (1976).
Yu. A. Azev andI. V. Teplyashina, Khim.-farm. Zh., No. 2, 42 (1998).
Yu. A. Azev, Mendeleev Commun., 164 (1997).
Yu. A. Azev,I. V. Teplyashina, andB. V. Golomolzin, Khim. Geterotsikl. Soedin., 1273 (1997).
A. Kreutzberger andE. Kreutzberger, Arch. Pharm. (Weinheim), 307, 836 (1974).
Yu. A. Azev andO. V. Gryazeva in Abstracts of the 13th International Conference on Organic Synthesis, Warsaw, Poland (2000), p. 126.
T. L. Jacobs, in R. C. Elderfield (editor), Heterocyclic Compounds, Vol. 5, Wiley, New York (1957), p. 45.
O. V. Gryazeva andYu. A. Azev, in Youth School on Organic Chemistry, Abstracts of Plenaries and Test Reports, Ekaterinburg (2000), p. 232.
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Azev, Y.A., Gryazeva, O.V. & Golomolzin, B.V. Azines and Their Acyclic Derivatives as Transferers of One-carbon Fragment in Reactions with Pyrazolones. Chemistry of Heterocyclic Compounds 39, 1478–1486 (2003). https://doi.org/10.1023/B:COHC.0000014412.48911.60
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DOI: https://doi.org/10.1023/B:COHC.0000014412.48911.60