A study was carried out on the domino transformations of tetrahydrobenzofuro[2,3-c]pyridines and tetrahydrobenzofuro[3,2-c]pyridines by the action of activated alkynes in methanol and acetonitrile. This reaction is a new method for the synthesis of spiro[benzofuropyridines] showing acetylcholinesterase inhibition activity.
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L. G. Voskressensky, A. V. Listratova, T. N. Borisova, S. A. Kovaleva, R. S. Borisov, and A. V. Varlamov, Tetrahedron, 64, 10443 (2008).
L. G. Voskressensky, A. V. Listratova, T. N. Borisova, G. G. Alexandrov, and A. V. Varlamov, Eur. J. Chem., 36, 6106 (2007).
L. G. Voskressensky, T. N. Borisova, I. S. Kostenev, L. N. Kulikova, and A. V. Varlamov, Tetrahedron Lett., 47, 999 (2006).
A. V. Varlamov, T. N. Borisova, L. G. Voskressensky, T. A. Soklakova, L. N. Kulikova, A. I. Chernysev, and G. G. Alexandrov, Tetrahedron Lett., 43, 6767 (2002).
L. G. Voskressensky, T. N. Borisova, L. N. Kulikova, A. V. Varlamov, M. Catto, C. Altomare, and A. Carotti, Eur. J. Org. Chem., 14, 3128 (2004).
L. G. Voskressensky, S. A. Kovaleva, T. N. Borisova, A. V. Listratova, A. B. Eresko, V. S. Tolkunov, and S. V. Tolkunov, Tetrahedron, 66, 9421 (2010).
J. W. Daly, I. L. Kale, C. W. Myers, T. Tokueyama, J. A. Waters, and B. Witkop, Proc. Natl. Acad. Sci. USA., 8, 1870 (1971).
F. Perron and K. F. Albizati, Chem. Rev., 89, 1617 (1989).
R. Hegnauer, in: Chemotaxonomie der Pflanzen, Vol. 3, Birkhauser, Basel (1964), p. 447.
M. Tada and K. Chiba, Agric. Biol. Chem., 48, 1367 (1984).
V. Martinez, O. Barbera, J. Sanchez-Parareda, and J. A. Marco, Phytochemistry, 26, 2619 (1987).
L. G. Voskressensky, S. A. Kovaleva, T. N. Borisova, A. B. Eresko, V. S. Tolkunov, S. V. Tolkunov, V. N. Khrustalev, and A. V. Varlamov, Synth. Commun., 42, 3337 (2012).
L. G. Voskressensky, T. N. Borisova, T. A. Soklakova, L. N. Kulikova, R. S. Borisov, and A. V. Varlamov, Lett. Org. Chem., 2, 18 (2005).
A. Musial, M. Bajda, and B. Malawska, Curr. Med. Chem., 14, 2654 (2007).
S. Rizzo, C. Rivière, L. M. Piazzi, A. Bisi, S. Gobbi, M. Bartolini, V. Andrisano, F. Morroni, A. Tarozzi, J. P. Monti, and A. Rampa, J. Med. Chem., 51, 2883 (2008).
G. Ellman, K. Courtney, V. J. Andres, and R. Featherstone, Biochem. Pharmacol., 7, 88 (1961).
A. Carotti, M. de Candia, M. Catto, T. N. Borisova, A. V. Varlamov, E. Méndez-Alvarez, R. Soto-Otero, L. G. Voskressensky, and C. Altomare, Bioorg. Med. Chem., 14, 7205 (2006).
N. F. Kucherova, L. A. Aksanova, L. M. Sharkova, and V. A. Zagorevskii, Khim. Geterotsikl. Soedin., 1469 (1971). [Chem. Heterocycl. Compd., 7, 1368 (1971)].
G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., A64, 112 (2008).
This work was carried out with the financial support of the Russian Foundation for Basic Research (grant No. 11-03-90407).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 995-1006, June, 2013.
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Voskressensky, L.G., Kovaleva, S.A., Borisova, T.N. et al. Recyclization of benzofuropyridines by the action of activated alkynes in the synthesis of spiro[benzofuropyridines], representatives of a new class of acetylcholinesterase inhibitors. Chem Heterocycl Comp 49, 930–940 (2013). https://doi.org/10.1007/s10593-013-1328-8
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DOI: https://doi.org/10.1007/s10593-013-1328-8