Abstract
N1-Phenyl- and N1-(3,5-dichloro-2-pyridyl)amidrazones have been synthesized by the reaction of imino esters of heterocyclic acids with phenyl- or (3,5-dichloro-2-pyridyl)hydrazine. Acylation of the products with acid chlorides leads to 1-phenyl- and 1-(3,5-dichloro-2-pyridyl)-3-hetaryl-5-R2-1H-1,2,4-triazoles. Compounds of this type are also formed by the condensation of N-acylimino esters of heterocyclic acids with phenyl- or (3,5-dichloro-2-pyridyl)hydrazine.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
REFERENCES
E. G. Marinicheva, A. D. Shebaldova, V. Yu. Chefranov, in: Chemistry and Technology of Furan Compounds, Intercollegiate Collection of Scientific Works, Krasnodar State Technological University, Krasnodar (1995), p. 85.
F. D. Popp, Eur. J. Med. Chem., 24, 313 (1989).
W. Kuzmierkiewicz, H. Foks, and M. Baranowsi, Sci. Pharm., 53, No. 3, 133 (1985).
C. A. Lipinski, J. L. LaMattina, and P. J. Oates, J. Med. Chem., 29, 2154 (1986).
S. P. Hiremath, N. N. Goudar, and M. G. Purohit, Indian J. Chem., 20B, 388 (1981).
V. K. Rastogi, V. K. Agarwal, J. N. Sinha, A. Chaudhari, and S. S. Parmar, Can. J. Pharm. Sci., 9, 107 (1974).
S. Bahadur, S. P. Singh, and M. K. Shukla, Arch. Pharm. (Weinheim, Ger.), 315, 312 (1982).
M. I. Husain and V. Kumar, Indian J. Chem., 31B, 673 (1992).
H. Ishikawa, T. Oono, K. Hirayama, and K. Kajikawa, Jpn. Patent 92164084; Chem. Abstr., 117, 186649 (1992).
P. Wegner, M. Krueger, G. Johann, R. Rees, J. Head, and G. Rowson, BDR Patent 3813886; Chem. Abstr., 112, 1984 25 (1990).
R. F. Aries, Fr. Patent 2248274; Chem. Abstr., 89, 179133 (1978).
V. I. Kelarev, R. A. Karakhanov, Yu. N. Polivin, and A. S. Remizov, Khim. Geterotsikl. Soedin., 1587 (1992).
V. I. Kelarev, V. N. Koshelev, and M. A. Silin, Zh. Org. Khim., 34, 1250 (1998).
V. I. Kelarev, M. A. Silin, N. A. Grigor'eva, and V. N. Koshelev, Khim. Geterotsikl. Soedin., 249 (2000).
M. A. Perez, S. A. Dorado, and J. L. Soto, Synthesis, 483 (1983).
V. I. Kelarev and V. N. Koshelev, Usp. Khim., 64, 339 (1995).
S. Patai (editor), The Chemistry of Amidines and Imidates, J. Wiley and Sons, London, New York, Sydney, Toronto (1975).
D. G. Neilson, R. J. Roger, J. W. M. Heatlie, and L. R. Newlands, Chem. Rev., 70, 151 (1970).
A. R. Katritzky (editor), Physical Methods in Heterocyclic Chemistry, Academic Press, New York (1963).
M. Dziewonska, Spectrochim. Acta, 23A, 1195 (1967).
V. A. Lopyrev, N. I. Chipanina, L. G. Rozinova, G. N. Sarapulova, R. G. Sultangareev, and M. G. Voronkov, Khim. Geterotsikl., Soedin., 1682 (1977).
E. Lukevics (editor), Advances in Furan Chemistry [in Russian], Zinatne, Riga (1978), p. 19.
P. J. Sundberg, The Chemistry of Indoles, Academic Press, New York (1970), p. 21.
R. A. Karakhanov, V. I. Kelarev, A. S. Kokosova, V. A. Malyshev, and V. I. Zav'yalov, Zh. Org. Khim., 28, 1750 (1992).
V. I. Kelarev and G. A. Shvekhgeimer, Khim. Geterotsikl. Soedin., 645 (1980).
N. A. Grigor'eva, Dissertation for Candidate of Chemical Sciences, Moscow (2000).
V. I. Kelarev, M. A. Silin, I. G. Kotova, K. I. Kobrakov, I. I. Rybina, and V. K. Korolev, Khim. Geterotsikl. Soedin., 243 (2003).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Kelarev, V.I., Silin, M.A., Kobrakov, K.I. et al. Synthesis of 1,3,5-Trisubstituted 1H-1,2,4-Triazoles Containing Hetaryl Fragments. Chemistry of Heterocyclic Compounds 39, 736–743 (2003). https://doi.org/10.1023/A:1025638910987
Issue Date:
DOI: https://doi.org/10.1023/A:1025638910987