Abstract
A series of N-ferrocenylalkyl pyrroles were synthesized by intermolecular redox amination of ferrocenyl ketones and formylferrocene with pyrroline. The racemic mixtures were separated into enantiomers using high performance liquid chromatography. The structure of N-ferrocenylmethylpyrrole was determined by X-ray diffraction.
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L. Weber, Curr. Med. Chem., 2002, 9, 2085.
C. Hulme, V. Core, Curr. Med. Chem., 2003, 10, 51.
T.-L. Su, T.-Ch. Lee, R. Kakadiya, Eur. J. Med. Chem., 2013, 69, 609.
P. Meunier, I. Quattara, B. Gautheron, J. Tirouflet, D. Camboli, J. Besanson, F. Boulay, Eur. J. Med. Chem., 1991, 26, 351.
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, K. G. Shitkov, Appl. Organomet. Chem., 1993, 7, 85.
L. V. Snegur, A. A. Simenel, Yu. S. Nekrasov, E. A. Morozova, Z. A. Starikova, S. M. Peregudova, Yu. V. Kuzmenko, V. N. Babin, L. A. Ostrovskaya, N. V. Bluchterova, M. M. Fomina, J. Organomet. Chem., 2004, 689, 2473.
L. V. Snegur, Yu. S. Nekrasov, N. S. Sergeeva, Zh. V. Zhilina, V. V. Gumenyuk, Z. A. Starikova, A. A. Simenel, N. B. Morozova, I. K. Sviridova, V. N. Babin, Appl. Organomet. Chem., 2008, 22, 139.
A. A. Simenel, S. V. Samarina, L. V. Snegur, Z. A. Starikova, L. A. Ostrovskaya, N. V. Bluchterova, M. M. Fomina, Appl. Organomet. Chem., 2008, 22, 276.
G. N. Yashchenko, A. A. Shashmurina, G. M. Anoshina, L. A. Gorelova, N. G. Evstigneeva, L. V. Alekseeva, L. B. Radina, Pharm. Chem. J. (Engl. Transl.), 1978, 12, 1317.[Khim.-Farm. Zh., 1978, 12, No. 10, 68].
D. A. Oparin, V. D. Makhaev, V. D. Vil’chevskaya, T. I. Zimatkina, Zh. V. Motylevich, S. M. Zimatkin, S. V. Zabrodskaya, A. I. Krylova, Yu. Yu. Gorelikova, Pharm. Chem. J. (Engl. Transl.), 1996, 30, 79.[Khim.-Farm. Zh., 1996, 30. No. 2, 11].
P. Köpf-Maier, H. Köpf, Chem. Rev., 1987, 87, 1137.
P. Köpf-Maier, Eur. J. Clinic. Pharm., 1994, 47, 1. 1.
V. N. Babin, P. M. Raevskii, K. G. Shitkov, L. V. Snegur, Yu. S. Nekrasov, Mendeleev Chem. J., 1995, 39, 17.
D. R. van Staveren, N. Metzler-Nolte, Chem. Rev., 2004, 104, 5931.
E. W. Neuse, J. Inorg. Organomet. Polym. Materials, 2005, 15, 3.
U. Schatzschneider, N. Metzler-Nolte, Angew. Chem., Int. Ed., 2006, 45, 1504.
G. Jaouen, S. Top, A. Vessières, G. Leclercq, M. J. McGlinchey, Curr. Med. Chem., 2004, 11, 2505.
A. Vessières, S. Top, W. Beck, E. Hillard, G. Jaouen, Dalton Trans., 2006, 529.
G. Tabbi, C. Cassino, G. Cavigiolio, D. Colangelo, A. Ghiglia, I. Viano, D. Osella, J. Med. Chem., 2002, 45, 5786.
H. Tamura, M. Miwa, Chem. Lett., 1997, 26, 1177.
A. A. Simenel, E. A. Morozova, L. V. Snegur, S. I. Zykova, V. V. Kachala, L. A. Ostrovskaya, N. V. Bluchterova, M. M. Fomina, Appl. Organomet. Chem., 2009, 23, 219.
O. Galangau, C. Dumas-Verdes, E. Yu, Schmidt, B. A. Trofimov, G. Clavier, Organometallics, 2011, 30, 6476.
T. L. Rose, A. B. Kon, Inorg. Chem., 1993, 32, 781.
S. Ramakrishnan, A. Srinivasan, Org. Lett., 2007, 23, 4769.
J. Chen, C. O. Too, G. G. Wallace, G. F. Swiegers, Electrochim. Acta, 2004, 49, 691.
A. B. Kon, J. S. Foos, T. L. Rose, J. Chem. Mater., 1992, 4, 416.
D. M. Panov, A. V. Polezhaev, A. V. Polukeev, P. V. Petrovskii, A. A. Koridze, Russ. Chem. Bull. (Int. Ed.), 2010, 59, 2098.[Izv. Akad. Nauk, Ser. Khim., 2010, 2045].
P. G. Cozzi, L. Zoli, Green Chem., 2007, 9, 1292.
D. W. Armstrong, W. DeMond, B. P. Czech, Anal. Chem., 1985, 57, 481.
A. A. Simenel, Yu. V. Kuzmenko, E. A. Morozova, M. M. Ilyin, I. F. Gun’ko, L. V. Snegur, J. Organomet. Chem., 2003, 688, 138.
A. A. Simenel, Yu. V. Kuz’menko, M. M. Il’in, V. V. Gumenyuk, L. V. Snegur, Yu. S. Nekrasov, Russ. Chem. Bull. (Int. Ed.), 2004, 53, 939.[Izv. Akad. Nauk, Ser. Khim., 2004, 901].
L. V. Snegur, V. I. Boev, Yu. S. Nekrasov, M. M. Ilyin, V. A. Davankov, Z. A. Starikova, A. I. Yanovsky, A. F. Kolomiets, V. N. Babin, J. Organomet. Chem., 1999, 580, 2615. 16.
A. A. Simenel, PhD Thesis, A. N. Nesmeyanov Institute of Organoelement Compounds of the RAS, Moscow, 2004, 84.pp. (in Russian)
P. C. Reeves, Org. Synth., 1977, 56, 28.
R. B. Woodward, M. Rosenblum, M. C. Whiting, J. Am. Chem. Soc., 1952, 74, 3458.
G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., 2008, 64, 112.
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Dedicated to Academician of the Russian Academy of Sciences Yu. N. Bubnov on the occasion of his 80th birthday and to the 60th anniversary of the foundation of A. N. Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2281–2284, October, 2014.
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Zherebker, K.Y., Rodionov, A.N., Il’in, M.M. et al. Synthesis and properties of N-ferrocenylalkylated pyrroles. Russ Chem Bull 63, 2281–2284 (2014). https://doi.org/10.1007/s11172-014-0735-z
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DOI: https://doi.org/10.1007/s11172-014-0735-z