Abstract
The use of 1,3-dicarbonyl compounds containing strong electron-withdrawing substituents (perfluoroalkyl, 4-nitrophenyl) at one of the carbonyl groups in reaction with hydrazine or its monosubstituted derivatives (4-nitro- and 2,4-dinitrophenylhydrazines) leads to the formation of stable intermediates for the synthesis of pyrazoles (5-hydroxy-2-pyrazolines) or their linear tautomers (hydrazones).
Similar content being viewed by others
REFERENCES
A. N. Kost, and I. I. Grandberg, Adv. Heterocycl. Chem., 6, 347 (1966).
J. Elguero and G. I. Iranzo, J. Chem. Res. (S), 120 (1990).
P. P. Kondrat'ev, Z. E. Skryabina, V. I. Saloutin, and L. M. Khalilov, Zh. Org. Khim., 28, 1380 (1992).
K. N. Zelenin, M. Yu. Malov, S. I. Yakimovich, P. B. Terent'ev, and A. G. Kalandarishvili, Zh. Org. Khim., 24, 426 (1988).
S. I. Selivanov, R. A. Bogatkin, and B. A. Ershov, Zh. Org. Khim., 17, 886 (1981).
S. I. Selivanov, R. A. Bogatkin, and B. A. Ershov, Zh. Org. Khim., 18, 909 (1982).
S. I. Selivanov, K. G. Golodova, Ya. A. Abbasov, and B. A. Ershov, Zh. Org. Khim., 20, 1494 (1984).
S. I. Selivanov, K. G. Golodova, and B. A. Ershov, Zh. Org. Khim., 22, 2073 (1986).
S. I. Yakimovich and K. N. Zelenin, Zh. Obshch. Khim., 65, 705 (1995).
K. N. Zelenin, V. V. Alekseev, and A. R. Tygysheva, Tetrahedron, 51, 11251 (1995).
S. I. Yakimovich, I. V. Zerova, K. N. Zelenin, V. V. Alekseev, and A. R. Tugusheva, Zh. Obshch. Khim., 66, 418 (1996).
K. N. Zelenin, V. V. Alekseev, O. B. Kuznetsova, A. G. Saminskaya, S. I. Yakimovich, and I. V. Zerova, Zh. Org. Khim., 35, 383 (1999).
K. N. Zelenin, V. V. Alekseev, V. A. Khrustalev, S. I. Yakimovich, V. N. Nikolaev, and N. V. Koshmina, Zh. Org. Khim., 20, 180 (1984).
A. B. Khudoyarov, Kh. T. Sharipov, V. G. Yusupov, and N. A. Parpiev, Koordinats. Khim., 13, 1113 (1987).
K. N. Zelenin, L. A. Khorseeva, V. V. Alekseev, O. V. Arapov, Z. M. Matveeva, V. G. Yusupov, M. M. Karimov, and N. A. Parpiev, Zh. Obshch. Khim., 59, 1191 (1989).
K. N. Zelenin, L. A. Khorseeva, and V. V. Alekseev, Khim.-Farm. Zh., 26, No. 5, 30 (1992).
K. N. Zelenin, M. Yu. Malov, I. P. Bezhan, V. A. Khrustalev, and S. I. Yakimovich, Khim. Geterotsikl. Soedin., 854 (1985).
K. N. Zelenin, M. Yu. Malov, I. P. Bezhan, V. A. Khrustalev, and S. I. Yakimovich, Khim. Geterotsikl. Soedin., 1000 (1985).
K. N. Zelenin, A. Yu. Ershov, M. Yu. Malov, and S. I. Yakimovich, Dokl. Akad. Nauk, 289, 1132 (1986).
K. N. Zelenin and S. I. Yakimovich (Yakimovitch), Targets Heterocycl. Syst., 2, 207 (1998); Chem. Abs., 131, 73578 (1999).
M. Yu. Malov, Thesis for Candidate of Chemical Sciences [in Russian], Leningrad (1988).
T. Nishiwaki, J. Chem. Soc., B, 885 (1967).
T. Nishiwaki, Bull. Chem. Soc. Japan, 42, 3024 (1969).
B. Sjollema, Liebigs Ann. Chem., 279, 249 (1894).
P. Yates and D. W. Farnum, Tetrahedron, 18, 881 (1962).
I. I. Grandberg, Vei-py Din, and A. N. Kost, Zh. Obshch. Khim., 30, 1373 (1960).
M. R. Grimmett, K. H. R. Lim, and R. T. Weaveas, Aust. J. Chem., 32, 2203 (1979).
C. Barat, J. Indian. Chem. Soc., 8, 801 (1931).
N. K. Kochketkov, E. D. Khomutova, O. B. Mikhailova, and A. N. Nesmeyanov, Izv. Akad. Nauk. Ser. Khim., 1181 (1957).
L. Knorr and G. Rosengarten, Liebigs Ann. Chem., 279, 237 (1894).
L. Knorr and B. Oettiger, Liebigs Ann. Chem., 279, 244 (1894).
L. Knorr and G. Rosengarten, Liebigs Ann. Chem., 279, 231 (1894).
O. L. Brady, J. Chem. Soc., 759 (1931).
D. M. Burness, J. Org. Chem., 21, 97 (1956).
K. Auwers and H. Stuhlmann, Berichte, 59, 1054 (1926).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Zelenin, K.N., Tugusheva, A.R., Yakimovich, S.I. et al. 5-Hydroxy-2-pyrazolines and Some of Their 1-Substituted Analogs. Chemistry of Heterocyclic Compounds 38, 668–676 (2002). https://doi.org/10.1023/A:1019909117505
Issue Date:
DOI: https://doi.org/10.1023/A:1019909117505