The alkylation of o-cyanophenol by 4-chloromethylcoumarins and subsequent intramolecular condensation by the cyano and methylene groups gives substituted 4-(3-amino-2-benzo-furanyl)coumarins. We studied the reactions of these compounds with acylating agents as well as with aldehydes, which lead to the 6H-[1]benzofuro[3,2-b]chromeno[4,3-d]pyridin-6-one system as the result of consecutive transformations.
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References
J. B. Harborne and H. Baxter (editors), Handbook of Natural Flavonoids, vols. 1, 2, John Wiley & Sons, New York (1999), 1768 pp.
G. A. Kuznetsova, Natural Coumarins and Furocoumarins [in Russian], Nauka, Leningrad (1967), 248 pp.
R. Maurya and P. P. Yadav, Nat. Prod. Rep., 22, 400 (2005).
J. B. Harborne and C. A. Williams, Phytochemistry, 55, 481 (2000).
G. M.Bolanda and D. M. X. Donnelly, Nat. Prod. Rep., 241 (1998).
S. Hanmantgad, M. Kulkarnti, V. Patil, P. Diwan, and D. Kulkarnti, Indian J. Chem., 25B, 779 (1986).
A. R. Deshpande, U. K. Joshi, and M. V. Paradkar, Indian J. Chem., 27B, 524 (1988).
I. A. Khan and M. V. Kulkarni, Indian J. Chem., 38B, 491 (1999).
I. A. Khan, M. V. Kulkarni, M. Gopal, M. S. Shahabuddin, and C.-M. Sun, Bioorg. Med. Chem. Lett., 15, 3584 (2005).
E. Schlittler and U. Spitaler, Tetrahedron Lett., 2911 (1978).
T. K. Liao, P. Wittek, and C. C. Cheng, J. Heterocycl. Chem., 13, 1283 (1976).
A. Court and V. Petrow, J. Chem. Soc., 334 (1952).
C. N. O'Callaghan, Synthesis, 5, 499 (1987).
T. R. Kelly and M. H. Kim, J. Org. Chem., 57, 1593 (1992).
R. C. Winneker, M. M. Wagner, and B. Singh, J. Med. Chem., 33, 129 (1990).
A. Sakurai, H. Midorikawa, and Y. Hashimoto, Bull. Chem. Soc. Jpn., 43, 2925 (1970).
A. Sakurai, H. Midorikawa, and Y. Hashimoto, Bull. Chem. Soc. Jpn., 44, 1677 (1971).
A. Sakurai, H. Midorikawa, and Y. Hashimoto, J. Org. Chem., 37, 1523 (1972).
A. Sakurai, Y. Motomura, and H. Midorikawa, Bull. Chem. Soc. Jpn., 46, 973 (1973).
D. W. Rangnekar and S. V. Dhamnaskar, J. Heterocycl. Chem., 25, 1767 (1988).
O. H. Hishmat, N. M. A. El-Ehrashi, and Sh. E. El-Naem, Synthesis, 12, 1075 (1982).
G. A. Reynolds, J. A. VanAllan, and C. C. Petropoulos, J. Heterocycl. Chem., 7, 1061 (1970).
C. F. Koelsch and S. A. Sundet, J. Am. Chem. Soc., 72, 1681 (1950).
Y. Fall, L. Santana, M. Teijeira, and E. Uriarte, Heterocycles, 41, 647 (1995).
R. Singh, R. P. Singh, and O. P. Malik, Indian J. Chem., 29B, 996 (1989).
M. S. Frasinyuk, V. I. Vinogradova, S. P. Bondarenko, and V. P. Khilya, Khim. Prirodn. Soedin., 5, 485 (2007).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1568-1579, October, 2009.
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Frasinyuk, M.S., Gorelov, S.V., Bondarenko, S.P. et al. Synthesis and properties of 4-(3-amino-2-benzofuranyl)-coumarins. Chem Heterocycl Comp 45, 1261–1269 (2009). https://doi.org/10.1007/s10593-010-0417-1
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DOI: https://doi.org/10.1007/s10593-010-0417-1