Abstract
A convenient method was developed for the synthesis of substituted 4-azolyl-1-arylbutanones from the available γ-chlorobutyrophenones by successive stages of transformation into ketals, alkylation of sodium imidazolate or 1,2,4-triazolate by the ketals in DMF, and removal of the ketal protection.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
REFERENCES
N. N. Mel'nikov, Pesticides. Chemistry, Technology, and Application [in Russian], Khimiya, Moscow (1987), 712 pp.
L. V. Moshkova (editor), Medicines that You Choose [Russian translation], Mir, Moscow (2000), p. 607.
Yu. F. Krylov (editor), Register of Drugs of Russia. Encyclopedia of Drugs [in Russian], RLS-2000, Moscow (2000), pp. 423, 987.
M. D. Mashkovskii, Drugs [in Russian], vol. 2, Novaya Volna, Moscow (2000), pp. 67, 49.
M. Begtrup and P. Larsen, Acta Chem. Scand., 44, 1050 (1990).
E. F. Godefroi, J. Heeres, J. van Cutsem, and P. A. J. Janssen, J. Med. Chem., 12, 784 (1969).
K. Iizuka, K. Akahane, D. Momose, M. Nakazawa, T. Tanauchi, M. Kauvamura, I. Okyama, I. Kajiwara, Y. Iguchi, T. Okada, K. Taniguchi, T. Miyamoto, and M. Hayashi, J. Med. Chem., 24, 1139 (1981).
P. A. J. Janssen, US Pat. 2997472; Chem. Abstr., 56, 11603 (1962).
J. P. Li and J. H. Biel, J. Med. Chem., 9, 917 (1969).
P. A. J. Janssen, C. Van de Westeringh, A. H. M. Jageneau, P. J. A. Demoen, B. K. F. Hermans, G. H. P. Van Daele, K. H. L. Schellekens, C. A. M. Van der Eycken, and C. J. E. Niemegeers, J. Med. Pharm. Chem., 1, 281 (1959).
W. Robertson, J. H. Krushinski, E. E. Beedle, J. D. Leander, D. T. Wong, and R. C. Rathbun, J. Med. Chem., 29, 1577 (1986).
S. Upadhyaya and L. Bauer, J. Heterocycl. Chem., 29, 1053 (1992).
E. Ya. Borisova, I. A. Rubtsov, L. A. Botova, A. S. Lukashov, and E. M. Cherkasova, Izv. Vuzov. Khimiya i Khim. Tekhnologiya, 366 (1977).
V. A. Sanin and A. F. Grapov, Pesticides. Handbook [in Russian], Tekhnika. Kiev (1985), p. 68.
O. Shigeru, J. Am. Chem. Soc., 78, 4030 (1956).
F. Thurkauf, A. E. Jacobson, and K. C. Rice, Synthesis, 233 (1998).
F. A. J. Meskens, Synthesis, 501 (1981).
T. W. Bentley, R. V. Jones, and P. J. Wareham, Tetrahedron Lett., 30, 4013 (1989).
M. Sharshunova, V. Shvarts, and Ch. Mikhalets, Thin-Layer Chromatography in Pharmacy and Clinical Biochemistry [Russian translation], vol. 2, Mir, Moscow (1980), p. 583.
Author information
Authors and Affiliations
Additional information
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1161–1167, August, 2005.
Rights and permissions
About this article
Cite this article
Karachev, D.A., Popkov, S.V. Synthesis of 1-Aryl-4-azolylbutanones. Chem Heterocycl Compd 41, 987–993 (2005). https://doi.org/10.1007/s10593-005-0265-6
Received:
Issue Date:
DOI: https://doi.org/10.1007/s10593-005-0265-6