Abstract
A new three-component reaction between salicylaldehydes, barbituric acid, pyrazolones, in the presence of para-toluenesulfonic acid, efficiently provides pyrazol-chromeno[2,3-d]pyrimidine-ones derivatives in good yields in ethanol/water at 70 °C. This multicomponent reaction showed high atom economy.
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Multicomponent Reactions ed. by J. Zhu, H. Bienaymé (Wiley, Weinheim, 2005)
Domino Reactions in Organic Synthesis ed. by L.F. Tietze, G. Brasche, K. Gericke (Wiley, Weinheim, 2006)
U. Dömling, I. Ugi, Angew. Chem. Int. Ed. 39, 3168–3210 (2000)
E. Soleimani, M.M. Khodaei, N. Batooie, M. Baghbanzadeh, Green Chem. 13, 566–569 (2011)
E. Soleimani, M. Zainali, J. Org. Chem. 76, 10306–10311 (2011)
E. Soleimani, M. Zainali, S. Samadi, Tetrahedron Lett. 52, 4186–4188 (2011)
E. Soleimani, M. Zainali, N. Ghasemi, B. Notash, Tetrahedron 69, 9832–9838 (2013)
B.S. Holla, M. Mahalinga, M.S. Karthikeyan, P.M. Akberali, N.S. Shetty, Bioorg. Med. Chem. 14, 2040–2047 (2006)
A.H. Shamroukh, M.E.A. Zaki, E.M.H. Morsy, F.M. Abdel-Motti, F.M.E. Abdel-Megeid, Arch. Pharm. Chem. Life Sci. 14, 340–345 (2007)
E. Akbas, I. Berber, Eur. J. Med. Chem. 40, 401–405 (2005)
R.Z. Yan, X.Y. Liu, W.F. Xu, C. Pannecouque, M. Witvrouw, E. DeClercq, Arch. Pharm. Res. 29, 957–962 (2006)
L.C. Chou, L.J. Huang, J.S. Yang, F.Y. Lee, C.M. Teng, S.C. Kuo, Bioorg. Med. Chem. 15, 1732–1740 (2007)
J. Li, Y.F. Zhao, X.L. Zhao, X.Y. Yuan, P. Gong, Arch. Pharm. Chem. Life Sci. 339, 593–597 (2006)
V. Krystof, D. Moravcova, M. Paprskarova, P. Barbier, V. Peyrot, A. Hlobilkova, L. Havlicek, M. Strnad, Eur. J. Med. Chem. 41, 1405–1411 (2006)
S. Schenone, O. Bruno, A. Ranise, F. Bondavalli, C. Brullo, P. Fossa, L. Mosti, G. Menozzi, F. Carraro, A. Naldini, C. Bernini, F. Manettic, M. Botta, Bioorg. Med. Chem. Lett. 14, 2511–2517 (2004)
G. Daidone, D. Raffa, B. Maggio, M.V. Raimondi, F. Plescia, D. Schillaci, Eur. J. Med. Chem. 39, 219–224 (2004)
S.C. Ren, F.Y. Sheau, M.L. Chih, G. Amooru, T.K. Damu, C.P. Cheng, F.B. Kenneth, L.K. Hsiung, W.T. Shung, Bioorg. Med. Chem. 17, 6137–6143 (2009)
A.V. Karnik, A.M. Kulkarni, N.J. Malviya, B.R. Mourya, B.L. Jadhav, Eur. J. Med. Chem. 43, 2615–2617 (2008)
K.J. Hwan, K.H. Eun, J.J. Kyung, K. Hwajung, C. Jungsook, L. Heesoon, Arch. Pharm. Res. 29, 728–734 (2006)
C. Fakher, M. Mehdi, B.M. Hedi, C. Leila, S. Mansour, Eur. J. Med. Chem. 42, 715–718 (2007)
C.Y. Cheng, H. Chiu, M.J. Chang, Y.C. Lin, M.C. Tsai, H.C. Yu, Bioorg. Med. Chem. Lett. 8, 463–468 (1998)
O.A. Abdou, H.E. Ahmed, A.A. Sayed, H.Z. Yasser, J. Sulf. Chem. 26, 405–410 (2005)
M.B. Deshmukh, S.M. Salunkhe, D.R. Patil, P.V. Anbhule, Eur. J. Med. Chem. 44, 2651–2654 (2009)
G. Cecile, D. Douguet, V. Huteau, M. Gilles, M.L. Helene, P. Sylvie, Bioorg. Med. Chem. 16, 6075–6085 (2008)
R. Lin, G. Sigmond, P.J. Johnson, S.K. Connolly, E. Wetter, T.V. Binnun, W.V. Hughes, N.B. Murray, S.J. Pandey, M.M. Mazza, A.R. Adams, F. Pesquera, A.M. Steven, Bioorg. Med. Chem. Lett. 19, 2333–2337 (2009)
E.P. da Silva Falcao, S.J. Melo, R.M. Srivastava, M.T. Catanho, S.C. Nascimento, Eur. J. Med. Chem. 41, 276–282 (2006)
Q. Chen, X. Zhu, L. Jiang, L.M. Yang, G. Fu, Eur. J. Med. Chem. 43, 595–603 (2008)
A. Agarwal, R. Ashutosh, N. Goyal, P.M.S. Chauhan, S. Gupta, Bioorg. Med. Chem. 13, 6678–6684 (2005)
E. Soleimani, S. Ghorbani, H.R. Ghasempour, Tetrahedron 69, 8511–8515 (2013)
X.J. Wang, J. Tan, K. Grozinger, Tetrahedron Lett. 41, 4713–4716 (2000)
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We gratefully acknowledge financial support from the Iran National Science Foundation (INSF) and Research Council of Razi University.
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Soleimani, E., Ghanbarian, M., Saei, P. et al. Synthesis of new derivatives of pyrazol-chromeno[2,3-d]pyrimidine-ones by a one-pot three-component reaction. J IRAN CHEM SOC 12, 2227–2232 (2015). https://doi.org/10.1007/s13738-015-0701-1
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DOI: https://doi.org/10.1007/s13738-015-0701-1