Abstract
Electrochemically initiated catalytic chain transformation of salicylaldehydes and CH acids containing the cyano group in an ethanolic solution in an undivided cell produced substituted 4H-chromenes in 85–95% yields.
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The Flavonoids — Advances in Research, Ed. J. B. Harbone, Chapman and Hall, London, 1988.
G. A. Iacobucci, J. G. Sweeny, Tetrahedron, 1983, 39, 3005.
B. A. Bohm, J. B. Choy, A. Y.-M. Lee, Phytochemistry, 1989, 28, 501.
M. Gill, Aust. J. Chem., 1995, 48, 1.
V. S. Parmar, S. C. Jain, K. S. Bisht, R. Jain, P. Taneja, A. Jha, O. D. Tyagi, A. K. Prasad, J. Wengel, C. E. Olsen, P. M. Boll, Phytochemistry, 1997, 46, 597.
V. V. Polyakov, Chem. Nat. Compd., 1999, 35, 21.
W. Sun, L. J. Cama, E. T. Birzin, S. Warrier, L. Locco, R. Mosley, M. L. Hammond, S. P. Rohrer, Bioorg. Med. Chem. Lett., 2006, 16, 1468.
A. V. Stachulski, N. G. Berry, A. C. L. Low, S. L. Moores, E. Row, D. C. Warhurst, I. S. Adagu, J.-F. Rossignol, J. Med. Chem., 2006, 49, 1450.
C. Garino, F. Bihel, N. Pietrancosta, Y. Laras, G. Quiliver, I. Woo, P. Klein, J. Bain, J.-L. Boucher, J.-L. Kraus, Bioorg. Med. Chem. Lett., 2005, 15, 135.
J. J. J. Leahy, B. T. Golding, R. J. Griffin, I. R. Hardcastle, C. Richardson, L. Rigoreau, G. C. M. Smith, Bioorg. Med. Chem. Lett., 2004, 14, 6083.
D. R. Anderson, S. Hedge, E. Reinhard, L. Gomez, W. F. Vernier, L. Lee, S. Liu, A. Sambandam, P. A. Snider, L. Masih, Bioorg. Med. Chem. Lett., 2005, 15, 1587.
J. Skommer, D. Wlodkowic, M. Mättöt Leukemia Res., 2006, 30, 322.
J. L. Wang, D. Liu, Z. Zhang, S. Shan, X. Han, S. M. Srinvasula, C. M. Croce, E. S. Alnemeri, Z. Huang, Proc. Natl. Acad. Sci. USA, 2000, 97, 7124.
E. C. Horning, M. G. Horning, J. Am. Chem. Soc., 1947, 69, 968.
W. Baker, C. S. Howes, J. Chem. Soc., 1953, 119.
G. P. Schiemenz, Chem. Ber., 1962, 95, 483.
S. Matsumura, Bull. Chem. Soc. Jpn, 1962, 35, 672.
H. Yasuda, H. Midorikawa, Bull. Chem. Soc. Jpn, 1966, 39, 1754.
A. Sakurai, H. Midorikawa, J. Org. Chem., 1969, 34, 3612.
A. Fujimoto, A. Sakurai, Synthesis, 1977, 871.
J. F. Roudier, A. Foucaud, Synthesis, 1984, 159.
M. Curini, F. Epifano, S. Chimichi, F. Montanari, M. Nocchetti, O. Rosati, Tetrahedron Lett., 2005, 46, 3497.
C. N. O’Callaghan, T. B. McMurry, J. E. O’Brein, J. Chem. Soc., Perkin Trans. 1, 1995, 417.
Organic Electrochemistry, Ed. H. Lund (4th ed.), Marcel Dekker Inc., New York, 2000.
Novel Trends in Electroorganic Synthesis, Ed. S. Torii, Springer, Berlin, 1998.
M. N. Elinson, S. K. Feducovich, T. L. Lizunova, G. I. Nikishin, Tetrahedron, 2000, 56, 3063.
M. T. Elinson, S. K. Feducovich, Z. A. Starikova, A. N. Vereshchagin, P. A. Belyakov, S. V. Gorbunov, G. I. Nikishin, Izv. Akad. Nauk, Ser. Khim., 2006, 102 [Russ. Chem. Bull., Int. Ed., 2006, 55, 106].
M. N. Elinson, A. S. Dorofeev, S. K. Feducovich, R. F. Nasybullin, S. V. Gorbunov, G. I. Nikishin, Electrochem. Commun., 2006, 8, 1567.
M. N. Elinson, A. S. Dorofeev, S. K. Feducovich, S. V. Gorbunov, R. F. Nasybullin, N. O. Stepanov, G. I. Nikishin, Tetrahedron Lett., 2006, 47, 7629.
S. Patai, Y. Israeli, J. Chem. Soc., 1960, 2025.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 582–587, March, 2008.
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Feducovich, S.K., Elinson, M.N., Dorofeev, A.S. et al. Electrocatalytic chain transformation of salicylaldehyde and CH acids into substituted 4H-chromenes. Russ Chem Bull 57, 595–600 (2008). https://doi.org/10.1007/s11172-008-0093-9
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DOI: https://doi.org/10.1007/s11172-008-0093-9