Abstract
Ferrocenylmethylation and α-ferrocenylethylation of indazole were carried out for the first time. Both reactions afforded two isomers, which were characterized by physical and physicochemical methods, among them by X-ray diffraction analysis. 1-(α-Ferrocenylethyl)indazole is thermally more stable than the 2-substituted isomer. Both isomers serve as ferrocenylalkylating agents with respect to s-triazole.
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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, 6 (Engl. Transl.)].
V. I. Boev, L. V. Snegur, V. N. Babin, and Yu. S. Nekrasov, Usp. Khim., 1997, 66, 874 [Russ. Chem. Rev., 1997, 66, 613 (Engl. Transl.)].
Yu. S. Nekrasov, Zh. V. Zhilina, V. V. Gumenyuk, L. V. Snegur, N. S. Sergeeva, and V. N. Babin, Zh. Vsesoyuz. Khim. Obshch. im. D. I. Mendeleeva, 1997, 41, 117 [Mendeleev Chem. J., 1997, 41, 172 (Engl. Transl.)].
L. V. Snegur, V. I. Boev, Yu. S. Nekrasov, M. M. Ilyin, V. A. Davankov, Z. A. Starikova, A. I. Yanovsky, A. F. Kolomiets, and V. N. Babin, J. Organomet. Chem., 1999, 580, 26.
L. V. Popova, V. N. Babin, R. B. Materikova, V. I. Boev, A. E. Snegireva, N. P. Borodina, G. M. Shaposhnikova, and O. B. Bychenko, Vth IUPAC Symp. Organomet. Chem. (Italy, Florence, 1989), p. 28.
L. V. Popova, V. N. Babin, Yu. A. Belousov, Yu. S. Nekrasov, A. E. Snegireva, N. P. Borodina, G. M. Shaposhnikova, O. B. Bychenko, P. M. Raevskii, N. B. Morozova, A. I. Ilyina, and K. G. Shcitkov, Appl. Organomet. Chem., 1993, 7, 85.
V. N. Babin, P. M. Raevskii, K. G. Shchitkov, L. V. Snegur, and Yu. S. Nekrasov, Zh. Vseross. Khim. Obshch. im. D. I. Mendeleeva, 1995, 39, 19 [Mendeleev Chem. J., 1995, 39, 17 (Engl. Transl.)].
Zh. V. Zhilina, V. V. Gumenyuk, Z. A. Starikova, A. I. Yanovsky, A. P. Pleshkova, D. V. Zverev, V. N. Babin, and Yu. S. Nekrasov, School_Conference for Young Scientists "Organometallic Chemistry towards the 21st Century," 100 Anniversary of Academician A. N. Nesmeyanov (Moscow, 6-11 September, 1999), Moscow, 1999, p. 9.
Comprehensive Heterocyclic Chemistry, Eds. A. R. Katritzky and Ch. W. Rees, Pergamon Press, New York, 1984, 5, 169-303.
A. H´Naifi, J.-M. Leger, and A. Carpy, Acta Crystallogr., Sect. C (Cryst. Struct. Commun.), 1986, 42, 339.
P. Fludzinski, D. A. Evrard, W. E. Bloomquist, W. B. Lacefield, W. Pfeifer, D. Jones, J. B. Deeter, and M. L. Cohen, J. Med. Chem., 1987, 30, 1535.
Cambrige Structural Database, April 2001.
Structure Correlation, Eds. H.-B. Burgi and J. D. Dunitz, VCH, Weinheim_New York, 1994, 2, pp. 767-784.
Zh. V. Zhilina, Ph. D. (Chem.) Thesis, A. N. Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences, Moscow, 1999, 130 pp. (in Russian).
A. Houlton, Ch. J. Isaak, A. E. Gibson, B. R. Horrocks, W. Clegg, and M. R. J. Elsegood, J. Chem. Soc., Dalton Trans., 1999, 3229.
Zh. V. Zhilina, V. V. Gumenyuk, Yu. S. Nekrasov, V. N. Babin, L. V. Snegur, Z. A. Starikova, and A. I. Yanovsky, Izv. Akad. Nauk, Ser. Khim., 1998, 1828 [Russ. Chem. Bull., 1998, 47, 1781 (Engl. Transl.)].
R. Huisgen and K. Bast, Organic Syntheses, 1962, 42, 62.
F. S. Arimoto and A. C. Haven, Jr., J. Am. Chem. Soc., 1955, 77, 6295.
SMART V5.051 and SAINT V5.00, Area Detector Control and Integration Software, 1998, Bruker AXS Inc., Madison, WI-53719, USA.
G. M. Sheldrick, SADABS, 1997, Bruker AXS Inc., Madi son, WI53719,USA.
G. M. Sheldrick, SHELXTL Ver. 5.0. Software Reference Manual, Siemens Industrial Automation, Inc., Madison, 1995.
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Gumenyuk, V.V., Starikova, Z.A., Nekrasov, Y.S. et al. Synthesis and properties of ferrocenylalkyl derivatives of indazole. Russian Chemical Bulletin 51, 1894–1899 (2002). https://doi.org/10.1023/A:1021360704054
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DOI: https://doi.org/10.1023/A:1021360704054