Abstract
Reactions of α-(1-benzotriazolyl)ethylferrocene (1) with 1,2,4-triazole, imidazole, benzimidazole, and edenine have been studied in the MeOH−HCl, MeOH, and AcOH systems. Compound 1 is a novel ferrocenylalkylating reagent which, unlike α-hydroxyalkylferrocenes, is capable of alkylating imidazole, benzimidazole (even in the absence of an acid catalyst), and adenine (regioselectively at the N(3) position). The antitumor activity discovered for ferrocenylalkylazoles of the type 1 may be attributed to the ability of such compounds to ferrocenylalkylate nucleic bases.
Similar content being viewed by others
References
N. S. Kochetkova, V. I. Boev, L. V. Popova, and V. N. Babin,Izv. Akad. Nauk SSSR, Ser. Khim., 1985, 1397 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1985,34, 1278 (Engl. Transl.)].
V. N. Babin, P. M. Raevskii, K. G. Shchitkov, L. V. Snegur, and Yu. S. Nekrasov,Zh. Ross. Khim. Obshch. im. D. I. Mendeleeva, 1995,39, 19 [Mendeleev. Chem. J., 1995,39, 17 (Engl. Transl.)].
V. I. Boev, D. Sci. (Chem.) Thes., Lipetsk State Ped. Inst., Lipetsk, 1993.
L. V. Snegur, Ph. D. (Chem.) Thes., INEOS RAN, Moscow, 1993.
V. I. Boev, P. M. Betankourt, L. V. Popova, and V. N. Babin,Zh. Obshch. Khim., 1991,61, 1651 [J. Gen. Chem. USSR, 1991,61 (Engl. Transl.)].
Shi-Chow Chen,J. Organomet. Chem., 1980,202, 183.
A. R. Katritzky and X. Lan,Chem. Soc. Rev., 1994,23, 363.
V. V. Gumenyuk, Zh. V. Zhilina, L. V. Snegur, and V. N. Babin,Tez. VI Vseross. konf. po metalloorganicheskoi khimii [VI All-Russian Conf. on Organometallic Chem., Abstrs.], Nizhnii Novgorod, 1995, 1995, Part 2, 373 (in Russian).
L. B. Townsend, R.K. Robins, R. N. Loeppky, and N. J. Leonard,J. Am. Chem. Soc., 1964,86, 5320.
A. E. Beasley and M. Rasmussen,Aust. J. Chem., 1981,34, 1107.
Author information
Authors and Affiliations
Additional information
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 172–174, January, 1997.
Rights and permissions
About this article
Cite this article
Gumenyuk, V.V., Zhilina, Z.V., Nekrasov, Y.S. et al. A novel ferrocenylalkylating reagent. Ferrocenylalkylation of imidazole and its derivatives. Russ Chem Bull 46, 168–170 (1997). https://doi.org/10.1007/BF02495368
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF02495368