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A novel and efficient one-pot method to Biginelli-like scaffolds

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Abstract

A novel and efficient one-pot method for the preparation of fused ring 3,4-dihydropyrimidin-2(1H)-ones and thiones from cyclocondensation of aldehydes, cyclic ketones and urea or thiourea using a catalytic amount of cupric chloride under mild conditions reaction is described. This new method has the advantage to give high yields, to be completed in short reaction times and simple product isolation procedure.

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References

  1. P. Biginelli, Gazz. Chim. Ital. 23 (1893) 360.

    Google Scholar 

  2. C.O. Kappe, Tetrahedron 49 (1993) 6937

    CAS  Google Scholar 

  3. b) E.H. Hu, D.R. Sidler, U.H. Dolling, J. Org. Chem. 63 (1998) 3454

    CAS  Google Scholar 

  4. Y. Ma, C. Qian, L. Wang, M. Yang, J. Org. Chem. 65 (2000) 3864

    CAS  Google Scholar 

  5. K. Ramalinga, P. Vijayalaximi, T.N.B. Kaimal, Synlett. (2001) 863

    Google Scholar 

  6. J. Lu, Y. Bai, L. Wang, B. Yang, H. Ma, Tetrahedron Lett. 41 (2000) 9075.

    CAS  Google Scholar 

  7. C.O. Kappe, Eur. J. Med. Chem. 35 (2000) 1043.

    CAS  Google Scholar 

  8. K.S. Atwal, B.N. Swanson, S.E. Unger, D.M. Floyd, S. Moreland, A. Hedberg, B.C. O’Reilly, J. Med. Chem. 34 (1991) 806

    CAS  Google Scholar 

  9. G.C. Rovnyak, K.S. Atwal, A. Hedberg, S.D. Kimball, S. Moreland, J.Z. Gougoutus, B.C. O’Reilly, J. Schwartz, M.F. Malley, J. Med. Chem. 35 (1992) 3254

    CAS  Google Scholar 

  10. G.J. Grover, S. Dzwonczyk, D.M. McMullen, D.E. Normandin, C.S. Parham, P.G. Sleph, S.J. Moreland, Pharmacol. 26 (1995) 289.

    CAS  Google Scholar 

  11. D. Nagarathnam, S.W. Miao, B. Lagu, G. Chiu, J. Fang, T.G.M. Dhar, J. Zhang, S. Tyagarajan, M.R. Marzabadi, F.Q. Zhang, W.C. Wong, W.Y. Sun, D. Tian, J.M. Wetzel, C. Forray, R.S.L. Chang, T.P. Broten, R.W. Ransom, T.W. Schorn, T.B. Chen, S. O’Malley, P. Kling, K. Schneck, R. Benedesky, C.M. Harrel, K.P. Vyas, C. Gluchowski, J. Med. Chem. 42 (1999) 4764

    CAS  Google Scholar 

  12. T.G. Murali Dhar, D. Nagarathnam, M.R. Marzabadi, B. Lagu, W.C. Wong, G. Chiu, S. Tyagarajan, S.W. Miao, F. Zhang, W. Sun, D. Tian, Q. Shen, J. Zhang, J.M. Wetzel, C. Forray, R.S.L. Chang, T.P. Broten, T.W. Schorn, T.B. Chen, S. O’Malley, R. Ransom, K. Sceneck, R. Bendesky, C.M. Harrell, K.P. Vyas, K. Zhang, J. Gilbert, D.J. Pettibone, M.A. Patane, M.G. Bock, R.M. Freidinger, C. Gluchowski, J. Med. Chem. 42 (1999) 4778.

    CAS  Google Scholar 

  13. M.A. Bruce, G.S. Pointdexter, G. Johnson, US 5,889,016, (1999).

  14. J. Lu, H.R. Ma, Synlett. (2000) 63

    Google Scholar 

  15. F. Bigi, S. Carloni, B. Frunllanti, R. Maggi, G. Sartori, Tetrahedron Lett. 40 (1999) 3465

    CAS  Google Scholar 

  16. V.R. Choudhary, V.H. Tillu, V.S Narkhede, H.B. Borate, R.D. Wakharkar, Catal. Commun. 4 (2003) 449.

    CAS  Google Scholar 

  17. Z. Hassani, M.R. Islami, M. Kalantari, Bio. Org. Med. Chem. Lett. 16 (2006) 4479.

    CAS  Google Scholar 

  18. J. Bussolari, P.A. McDonnell, J. Org. Chem. 65 (2000) 6777.

    CAS  Google Scholar 

  19. Y.L. Zhu, S.L. Huang, Y.J. Pan, Eur. J. Org. Chem. (2005) 2354.

    Google Scholar 

  20. M.M. Abelman, S.C. Smith, D.R. James, Tetrahedron Lett. 44 (2003) 4559

    CAS  Google Scholar 

  21. b) J. Azizian, A.A. Mohammadi, A.R. Karimi, M.R. Mohammadizadeh, Appl. Catal. A-Gen. 300 (2006) 85

    CAS  Google Scholar 

  22. J.C. Rodriguez-Dominguez, D. Bernardi, G. Kirsch, Tetrahedron Lett. 48 (2007) 5777.

    CAS  Google Scholar 

  23. Z.T. Wang, L.W. Xu, C.G. Xia, H.Q. Wang, Tetrahedron Lett. 45 (2004) 7951

    CAS  Google Scholar 

  24. b) Z.T. Wang, L.W. Xu, C.G. Xia, H.Q. Wang, Tetrahedron Lett. 47 (2006) 1361

    CAS  Google Scholar 

  25. G. Sabitha, K.B. Reddy, R. Srinivas, J.S. Yadav, Helv. Chim. Acta 88 (2005) 2996

    CAS  Google Scholar 

  26. B. Liang, X. Wang, J.-X. Wang, Z. Du, Tetrahedron 63 (2007) 1981.

    CAS  Google Scholar 

  27. M. Mirza-Aghayan, M. Bolourtchian, M. Hoseini, Synth. Commun. 34 (2004) 3335

    CAS  Google Scholar 

  28. M. Mirza-Aghayan, A. Moradi, M. Bolourtchian, R. Boukherroub, Synth. Commun. 40 (2010) 8.

    CAS  Google Scholar 

  29. P.H. Lee, H.A.K. Lee, S. Sung, S. Kim, Tetrahedron Lett. 42 (2001) 37

    CAS  Google Scholar 

  30. T. Ito, Y. Ishino, T. Mizuno, A. Iswkawa, J. Kobayashi, Synlett (2002) 2116

    Google Scholar 

  31. M. Bandini, M. Fagioli, A. Melloni, A. Umani-Ronchi, Synthesis (2003) 397.

    Google Scholar 

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Authors and Affiliations

  1. Chemistry and Chemical Engineering Research Center of Iran (CCERCI), P. O. BOX 14335-186, Tehran, Iran

    M. Mirza-Aghayan, A. Moradi & M. Bolourtchian

Authors
  1. M. Mirza-Aghayan
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  2. A. Moradi
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  3. M. Bolourtchian
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Correspondence to M. Mirza-Aghayan.

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Mirza-Aghayan, M., Moradi, A. & Bolourtchian, M. A novel and efficient one-pot method to Biginelli-like scaffolds. JICS 7, 269–274 (2010). https://doi.org/10.1007/BF03245888

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  • DOI: https://doi.org/10.1007/BF03245888

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