The reaction of natural isoflavones formononetin and cladrin with primary amines and formalin in the presence of a base catalyst was studied. Several novel substituted 9,10-dihydro-4H,8H-chromeno [8,7-e][1,3]oxazin-4-ones containing alkyl, benzyl, or heterylalkyl substituents in the N-9 position were synthesized.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
A. L. Kazakov, V. P. Khilya, V. V. Mezheritskii, and D. Litkei, Natural and Modified Isoflavonoids [in Russian], Izd. RGU, Rostov-on-Don, 1985.
E. T. Bailey, Aust. J. Agric. Res., 22, 731 (1971).
M. Shamma, Tetrahedron, 25, 3887 (1969).
J. Torel, J. Gillard, and P. Gillard, Phytochemistry, 25, 383 (1986).
P. Da Re, L. Verlicchi, and I. Setniker, J. Med. Chem., 10, 266 (1966).
C. Ito, M. Itoigawa, H. T. W. Tan, H. Tokuda, X. Y. Mou, T. Mukainaka, T. Ishikawa, H. Nishino, and H. Furukawa, Cancer Lett., 152, 187 (2000).
L. Denis, M. S. Morton, and K. Griffiths, Eur. Urol., 35, 377 (1999).
M. T. Siddiqui and M. Siddiqui, Lipids, 11, 243 (1976).
S. Yahara, T. Ogata, and R. Saijo, Chem. Pharm. Bull., 37, 979 (1989).
G. N. Dorofeenko, A. L. Shinkarenko, L. I. Lisevitskaya, V. V. Mezheritskii, A. L. Kazakov, and Yu. A. Zhdanov, Nauchn. Dokl. Vyssh. Shk. Biol. Nauki, 3, 35 (1975).
S. P. Bondarenko, M. S. Frasinyuk, and V. P. Khilya, Khim. Prir. Soedin., 273 (2003).
S. P. Bondarenko, M. S. Frasinyuk, and V. P. Khilya, Khim. Prir. Soedin., 277 (2003).
M. Tramontini, Synthesis, 12, 703 (1973).
R. B. Desai, J. Org. Chem., 26, 5251 (1961).
M. G. Patel and S. Sethna, J. Indian Chem. Soc., 39, 595 (1962).
D. R. Shridhar, C. V. R. Sastry, B. Lal, G. S. Raddi, K. K. Bhopale, R. S. Khokar, and K. Tripathi, Indian J. Chem., Sect. B, 19, 1065 (1980).
J. N. Gadre and P. S. Raote, Indian J. Chem., Sect. B, 32, 1285 (1993).
I. V. Nagorichna, M. M. Garazd, Ya. L. Garazd, and V. P. Khilya, Khim. Prir. Soedin., 14 (2007).
M. M. Garazd, Ya. L. Garazd, A. S. Ogorodniichuk, V. V. Shilin, A. M. Zhivolup, A. V. Turov, and V. P. Khilya, Khim. Prir. Soedin., 632 (1998).
A. Pelter and S. Foot, Synthesis, 5, 326 (1976).
A. S. Kukla and T. R. Seshadri, Indian J. Chem., 1, 343 (1963).
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 418–421, July–August, 2009.
Rights and permissions
About this article
Cite this article
Bondarenko, S.P., Frasinyuk, M.S. & Khilya, V.P. Aminomethylation of formononetin and cladrin by primary amines. Chem Nat Compd 45, 492–495 (2009). https://doi.org/10.1007/s10600-009-9400-4
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10600-009-9400-4