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A novel ferrocenylalkylating reagent. Ferrocenylalkylation of imidazole and its derivatives

  • Organometallic Chemistry
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Russian Chemical Bulletin Aims and scope

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.

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References

  1. 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.)].

    Google Scholar 

  2. 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.)].

    CAS  Google Scholar 

  3. V. I. Boev, D. Sci. (Chem.) Thes., Lipetsk State Ped. Inst., Lipetsk, 1993.

  4. L. V. Snegur, Ph. D. (Chem.) Thes., INEOS RAN, Moscow, 1993.

  5. 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.)].

    CAS  Google Scholar 

  6. Shi-Chow Chen,J. Organomet. Chem., 1980,202, 183.

    Article  CAS  Google Scholar 

  7. A. R. Katritzky and X. Lan,Chem. Soc. Rev., 1994,23, 363.

    Article  CAS  Google Scholar 

  8. 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).

  9. L. B. Townsend, R.K. Robins, R. N. Loeppky, and N. J. Leonard,J. Am. Chem. Soc., 1964,86, 5320.

    Article  CAS  Google Scholar 

  10. A. E. Beasley and M. Rasmussen,Aust. J. Chem., 1981,34, 1107.

    Article  CAS  Google Scholar 

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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 172–174, January, 1997.

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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

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  • DOI: https://doi.org/10.1007/BF02495368

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