The reaction of substituted 3-cinnamoyl-4-hydroxycoumarins with pyridinium salts of various bromomethyl ketones gives the corresponding 4-hydroxy-3-pyridylcoumarins. The use of microwave radiation decreases the time required and improves the yield of this reaction. The products obtained do not display solvatochromic properties or photochemical activity.
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References
R. S. Overman, J. Biol. Chem., 153, 5 (1944).
R. M. Dean, Naturally Occurring Oxygen Ring Compounds, Butterworth, London (1963).
M. Kuroda, D. Yoshida, and S. Mizusaki, Agric. Biol. Chem., 50, 243 (1986).
D. L. Rector, G. A. Conder, and S. D. Folz, US Pat. 8706.133; http://ep.espacenet.com/numberSearch?locale=_EP
R. S. Overman, M. A. Stahmann, C. F. Huebner, W. R. Sullivan, L. Spero, D. G. Doherty, M. Ikawa, L. Graf, S. Roseman, and K. P. Link, J. Biol. Chem., 153, 5 (1944).
R. B. Silverman, J. Am. Chem. Soc., 103, 3910 (1981).
K. P. Link and H. R. Eisenhauer, J. Am. Chem. Soc., 75, 2046 (1953).
V. F. Traven, I. V. Ivanov, A. S. Pavlov, A. V. Manaev, I. V. Voevodina, and V. A. Barachevskii, Mendeleev Commun., 17, 345 (2007).
E. C. Constable, M. D. Ward, and D. A. Tocher, J. Chem. Soc., Dalton Trans., 1675 (1991).
D. A. Bardwell, J. C. Jeffery, and M. D. Ward, Inorg. Chim. Acta, 236, 125 (1995).
D. A. Bardwell, J. C. Jeffery, and M. D. Ward, J. Chem. Soc., Dalton Trans., 3071 (1995).
C. A. Otter, D. A. Bardwell, S. M. Couchman, J. C. Jeffery, J. P. Maher, and M. D. Ward, Polyhedron, 17, 211 (1998).
H. Tanaka, S. Tokito, Y. Taga, and A. Okada, J. Mater. Chem., 8, 1999 (1998).
D. J. Brahmbhatt, G. B. Raolji, and S. U. Pandya, Indian. J. Chem., 38B, 212 (1999).
W. Zecher and F. Kröhnke, Chem. Ber., 94, 690 (1961).
V. F. Traven, O. B. Safronova, L. I. Vorob'eva, T. A. Chibisova, and I. N. Senchenya, Zh. Obshch. Khim., 70, 847 (2000).
V. F. Traven, A. V. Manaev, T. A. Chibisova, O. B. Safronova, K. A. Lysenko, and M. Yu. Antipin, Zh. Obshch. Khim., 70, 853 (2000).
Y. S. Chen, P. Y. Kuo, T. L. Shie, and D. Y. Yang, Tetrahedron, 62, 9410 (2006).
M. J. S. Dewar, E. G. Zeobisch, E. F. Healy, and J. J. P. Stewart, J. Am. Chem. Soc., 107, 3902 (1985).
F. M. Grazia, G. Chiarelotto, and G. Malesani, J. Heterocycl. Chem., 26, 245 (1989).
A. V. Manaev, T. A. Chibisova, and V. F. Traven, Izv. Akad. Nauk, Ser. Khim., 2144 (2006).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1800–1805, December, 2009.
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Manaev, A.V., Voevodina, I.V. & Traven, V.F. Synthesis and structure of 4-hydroxy-3-pyridylcoumarins. Chem Heterocycl Comp 45, 1449–1454 (2009). https://doi.org/10.1007/s10593-010-0448-7
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DOI: https://doi.org/10.1007/s10593-010-0448-7