Abstract
The interaction of salts of imidazole, 1,2,4-triazole, benzimidazole, and 2-benzylbenzimidazole with γ-butyrolactone has been studied. Ab initio quantum-chemical calculations showed a preference for N-alkylation on interaction of azolates with γ-butyrolactone.
Similar content being viewed by others
References
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).
T. Kamijo, R. Yamamoto, H. Harada, and K. Iizuka, Chem. Pharm. Bull., 312, 1213 (1983).
M. Varasi, G. Tarzia, F. Luzzani, L. Gallico, and D. Barone, Farmaco, 42, 425 (1987).
S. V. Sibiryak, Yu. V. Sorokin, R. F. Sadykov, and V. M. Dianov, Khim.-farm. Zh., 24, No. 11, 19 (1990).
V. N. Zhuravlev, S. V. Popkov, E. G. Lobanova, and A. L. Aleekseenko, in XII Russian National Congress “Man and Medicine”, Abstracts, Moscow (2005), p. 753.
K. Iizuka and K. Akahane, GB Patent 2016452; Chem. Abstr., 93, 114514 (1980).
O. K. Shevchenko, A. T. Ayupova, and G. G. Galust’yan, Khim. Geterotsikl. Soedin., 1491 (1992). [Chem. Heterocycl. Comp., 28, 1274 (1992)].
B. R. Lahue, S.-M. Lo, Z.-K. Wan, G. H. Woo, and J. K. Snyder, J. Org. Chem., 69, 7171 (2004).
J.-H. Li and J. K. Snyder, J. Org. Chem., 58, 516 (1993).
S. C. Denson, J.-H. Li, and J. K. Snyder, J. Org. Chem., 57, 5285 (1992).
H. Krzikalla and W. Alt, DR Patent 743661; Chem. Zentralblatt, 115, 1152 (1944).
H. Haussmann and H. Kaltschmidt, DB Patent 882093; Chem. Zentralblatt, 125, 10133 (1954).
T. W. Bentley, L. M. Howle, and P. J. Wareham, Tetrahedron, 48, 7869 (1992).
V. I. Minkin, B. Ya. Simkin, and R. M. Minyaev, Theory of Molecular Structure [in Russian], Feniks, Rostov-on-Don (1997), p. 237.
HyperChem 6.03. Trial Version. http://www.hyper.com
M. Sharshunova, V. Shvarts, and Ch. Mikhalets, Thin-Layer Chromatography in Pharmacy and Clinical Biochemistry, Part 2 [Russian translation], Mir, Moscow (1980), p. 583.
D. A. Karachev and S. V. Popkov, Khim. Geterotsikl. Soedin., 1161 (2005). [Chem. Heterocycl. Comp., 41, 987 (2005)].
A. Baba, N. Kawamura, H. Makina, Y. Ohta, S. Taketomi, and T. Sohda, J. Med. Chem., 39, 5176 (1996).
Author information
Authors and Affiliations
Corresponding author
Additional information
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6. pp. 910–916, June, 2007.
Rights and permissions
About this article
Cite this article
Alekseenko, A.L., Popkov, S.V. Preparation of 4-(azol-1-yl)butyric acids by the interaction of azoles with γ-butyrolactone. Chem Heterocycl Compd 43, 769–775 (2007). https://doi.org/10.1007/s10593-007-0124-8
Received:
Issue Date:
DOI: https://doi.org/10.1007/s10593-007-0124-8