Benzoxazine derivatives are typically synthesized by condensation reaction of a phenol with two equivalents of formaldehyde and various primary amines (aliphatic or aromatic) as starting materials either by employing solution or solvent-free conditions. In this work, coumarin Mannich bases were synthesized using 7-hydroxycoumarin as phenol and were obtained with moderate to very good yields.
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A. Schonberg and N. Latif, J. Am. Chem. Soc., 76, 6208 (1954).
A. K. Mitra, S. K. Misra, and A. Patra, Synth. Commun., 10, 915 (1980).
L. A. Singer and N. P. Kong, J. Am. Chem. Soc., 88, 5213 (1966).
O. Kayser and H. Kolodziej, Planta Med., 63, 508 (1997).
C. J. Wang, Y. J. Hsieh, C. Y. Chu, Y. L. Lin, and T. H. Tseng, Cancer Lett., 183, 163 (2002).
G. J. Fan, W. Mar, M. K. Park, E. Wook Choi, K. Kim, and S. Kim, Bioorg. Med. Chem. Lett., 11, 2361 (2001).
S. Kirkiacharian, D. T. Thuy, S. Sicsic, R. Bakhchinian, R. Kurkjian, and T. Tonnaire, Farmaco, 57, 703 (2002).
H. Mostafavi, R. Najjar, and E. Maskani, Chem. Nat. Compd., 49, 423 (2013).
I. V. Nagorichna, M. M. Garazd, Ya. L. Garazd, and V. P. Khilya, Chem. Nat. Compd., 43, 15 (2007).
S. P. Bondarenko, M. S. Frasinyuk, and V. P. Khilya, Chem. Nat. Compd., 45, 492 (2009).
S. P. Bondarenko, M. S. Frasinyuk, and V. P. Khilya, Chem. Heterocycl. Comp., 46, 529 (2010).
W. J. Burk, E. L. M Glennie, and C. Weatherbee, J. Org. Chem., 29, 909 (1964).
A. F. McDonagh and H. E. Smith, J. Org. Chem., 33, 1 (1968).
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Published in Khimiya Prirodnykh Soedinenii, No. 6, November–December, 2017, pp. 876–877.
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Ali-Asgari, S., Moradi, M., Maskani, E. et al. Synthesis and Characterization of Novel Heterocyclic Compounds Containing the Benzoxazine Ring by 7-Hydroxycoumarin. Chem Nat Compd 53, 1028–1030 (2017). https://doi.org/10.1007/s10600-017-2194-x
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DOI: https://doi.org/10.1007/s10600-017-2194-x