Abstract
The interaction of 3,5-dichloro-2-pyridylhydrazine with α,β-unsaturated carbonyl compounds leads to 1-(3,5-dichloro-2-pyridyl)-3,5-disubstituted Δ2-pyrazolines. It was shown that N-(3,5-dichloro-2-pyridyl)hydrazones of the corresponding aldehydes and ketones are formed as intermediates. Condensation of the hydrazine mentioned above with α,β-diketones gives 1,3,5-trisubstituted pyrazoles, but with acetoacetic ester a 1,3-disubstituted pyrazol-5-one containing a 3,5-dichloropyridyl residue is obtained.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
REFERENCES
K. I. Kobrakov, V. K. Korolev, I. I. Rybina, and V. I. Kelarev, Khim. Geterotsikl. Soedin., 1066 (2000).
I. G. Mikhailyuchenko, in Chemistry and Technology of Furan Compounds, Intercollegiate Collection of Scientific Works, Krasnodar State Technological University, Krasnodar (1988), p. 64.
L. K. Kulikova and L. V. Cherkesova, Khim.-farm. Zh., No. 3, 18 (1974).
F. Piozzi and C. Fuganti, Ann. Chim. (Rome), 57, 486 (1967).
S. Tripathi, B. R. Pandey, J. P. Barthwal, K. Kishor, and K. P. Bhargawa, Indian J. Physiol. Pharmacol., 24, 155 (1980).
K. Raman, B. R. Pandey, J. P. Barthwal, and S. S. Parmar, Eur. J. Med. Chem.-Chim. Ther., 15, 567 (1980).
V. I. Kelarev and G. A. Shvekhgeimer, Khim. Geterotsikl. Soedin., 147 (1986).
K. A. Thakar and A. M. Padhye, J. Indian Chem. Soc., 62, 465 (1985).
M. Z. A. Badr, A. M. Mahmoud, S. A. Mahgoub, and Z. A. Hozien, Bull. Chem. Soc. Jpn., 61, 1339 (1988).
S. P. Singh, I. Prakash, R. K. Tomer, O. Prakash, and S. N. Sawhney, Indian J. Chem., B22, 43 (1983).
S. P. Singh, D. R. Kodali, I. Prakash, O. Prakash, and S. N. Sawhney, Indian J. Chem., B23, 125 (1984).
J. Gante, H. Radunz, H. Eckart, D. Orth, K. Minck, A. Wild, and M. Klockow, Ger. Offen. 2906252; Chem. Abstr., 94, 192323 (1981).
S. Yamamoto, T. Kakuta, T. Sato, K. Morimoto, E. Oya, T. Ikai, and T. Nawamaki, Eur. Pat. Appl. 189069; Chem. Abstr., 105, 191075 (1986).
Z. Brzozowski and I. Kozakiewicz, Acta Pol. Pharm., 37, 601 (1980).
N. I. Mel'nikov, Pesticides [in Russian], Khimiya, Moscow (1987).
V. G. Kartsev, in Chemistry and Technology of Pyridine-Containing Pesticides, Proceedings of the All-Union Conference, Chernogolovka (1988), p. 9.
K. I. Kobrakov, V. I. Kelarev, I. I. Rybina, and V. K. Korolev, in Chemical Reactants, Reagents, and Processes of Low-Tonnage Chemistry, Abstracts XIII International Scientific and Technological Conference, Tula (2000), p. 95.
V. I. Kelarev, M. A. Silin, I. G. Kotova, K. I. Kobrakov, I. I. Rybina, and V. K. Korolev, Khim. Geterotsikl. Soedin., 243 (2003).
V. I. Kelarev, M. A. Silin, K. I. Kobrakov, I. I. Rybina, and V. K. Korolev, Khim. Geterotsikl. Soedin., 173 (2000).
K. Sasse, M. Hammond, F. Seuter, E. Perzborn, B. Pelster, G. Sturton, and T. Abram (A.-G. Bayer), Ger. Offen. DE 3443308; Chem. Abstr., 105, 153057 (1986).
O. Schallner, R. Gehring, and J. Stetter (A.-G. Bayer), Ger. Offen. DE 3520330; Chem. Abstr., 106, 156458 (1987).
A. N. Kost and V. V. Ershov, Usp. Khim., 4, 431 (1958).
S. Beech, J. Turnbull, and W. Wilson, J. Chem. Soc., 4686 (1952).
Yu. P. Kitaev and B. I. Buzykin, Hydrazones [in Russian], Nauka, Moscow (1974).
R. M. Silverstein, G. C. Bassler, and T. I. Morrill, Spectrometric Identification of Organic Compounds [Russian translation], Mir, Moscow (1977).
A. R. Katritzky (editor), Physical Methods in Heterocyclic Chemistry, Academic Press, New York (1963).
A. Junker, Nuclear Magnetic Resonance in Organic Chemistry [Russian translation], Mir, M oscow (1974), p. 71.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Kobrakov, K.I., Rybina, I.I., Kelarev, V.I. et al. Halogen-containing Pyridines. 8. Synthesis of 3,5-Dichloropyridines Containing Pyrazole and Pyrazoline Residues in Position 2. Chemistry of Heterocyclic Compounds 39, 749–755 (2003). https://doi.org/10.1023/A:1025643011896
Issue Date:
DOI: https://doi.org/10.1023/A:1025643011896