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First catalyst- and solvent-free synthesis of 3,4-dihydropyrimidin-2(1H)-ones and -thiones

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Abstract

A completely green and environmentally benign Biginelli synthesis of 3,4-dihydropyrimidine-2(1H)-ones and -thiones by one-pot three-component reaction of aromatic aldehydes with ethyl acetoacetate and urea or thiourea without any catalyst under solvent-free conditions is described.

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References

  1. Kappe, C.O., Tetrahedron, 1993, vol. 49, p. 6937.

    Article  CAS  Google Scholar 

  2. Kappe, C.O., Fabian, W.M.F., and Semones, M.A., Tetrahedron, 1997, vol. 53, p. 2803

    Article  CAS  Google Scholar 

  3. Atwal, K.S., Rovnyak, G.C., Kimball, S.D., Floyd, D.M., Moreland, S., Swanson, B.N., Gougoutas, J.Z., Schwartz, J., Smillie, K.M., and Malley, M.F., J. Med. Chem., 1990, vol. 33, p. 2629

    Article  CAS  Google Scholar 

  4. Rovnyak, G.C., Kimball, S.D., Beyer, B., Cucinotta, G., DiMarco, J.D., Gougoutas, J.Z., Hedberg, A., Malley, M.F., McCarthy, J.P., Zhang, R., and Moreland, S., J. Med. Chem., 1995, vol. 38, p. 119

    Article  CAS  Google Scholar 

  5. Atwal, K.S., Swanson, B.N., Unger, S.E., Floyd, D.M., Moreland, S., Hedberg. A., and O’Reilly, B.C., J. Med. Chem., 1991, vol. 34, p. 806

    Article  CAS  Google Scholar 

  6. Kappe, C.O., Eur. J. Med. Chem., 2000, vol. 35, p. 1043

    Article  CAS  Google Scholar 

  7. Brands, M., Grande, Y.C., Endermann, R., Gahlmann, R., Kruger, J., and Raddatz, S., Bioorg. Med. Chem. Lett., 2003, vol. 13, p. 2641.

    Article  CAS  Google Scholar 

  8. Heys, L., Moore, C.G., and Murphy, P.J., Chem. Soc. Rev., 2000, vol. 29, p. 57

    Article  CAS  Google Scholar 

  9. Patil, A.D., Kumar, N.V., Kokke, W.C., Bean, M.F., Freyer, A.J., de Brosse, C., Mai, S., Truneh, A., Faulkner, D.J., Carte, B., Breen, A.L., Hertzberg, R.P., Johnson, R.K., Westley, J.W., and Potts, B.C.M., J. Org. Chem., 1995, vol. 60, p. 1182.

    Article  CAS  Google Scholar 

  10. Biginelli, P., Gazz. Chim. Ital., 1893, vol. 23, p. 360.

    Google Scholar 

  11. Lu, J. and Ma, H., Synlett, 2000, p. 63.

    Google Scholar 

  12. Hu, E.H., Sidler, D.R., and Dolling, U.H., J. Org. Chem., 1998, vol. 63, p. 3454.

    Article  CAS  Google Scholar 

  13. Tu, S., Fang, F., Zhu, S., Li, T., Zhang, X., and Zhuang, Q., Synlett, 2004, p. 537.

    Google Scholar 

  14. Dilmaghani, K.A., Zeynizadeh, B., and Yari, M., Phosphorus, Sulfur Silicon Relat. Elem., 2009, vol. 184, p. 1722.

    Article  CAS  Google Scholar 

  15. Salehi, P., Dabiri, M., Zolfigol, M.A., and Bodaghifard, M.A., Tetrahedron Lett., 2003, vol. 44, p. 2889.

    Article  CAS  Google Scholar 

  16. Kuarm, B.S., Madhav, J.V., Laxmi, S.V., and Rajitha, B., Synth. Commun., 2012, vol. 42, p. 1211.

    Article  CAS  Google Scholar 

  17. Lu, J. and Bai, Y., Synthesis, 2002, p. 466.

    Google Scholar 

  18. Xu, F., Wang, J.-J., and Tian, Y.-P., Synth. Commun., 2008, vol. 38, p. 1299.

    Article  CAS  Google Scholar 

  19. Lu, J., Bai, Y., Wang, Z., Yang, B., and Ma, H., Tetrahedron Lett., 2000, vol. 41, p. 9075.

    Article  CAS  Google Scholar 

  20. Reddy, C.V., Mahesh, M., Raju, P.V.K., Babu, R., and Reddy, V.V.N., Tetrahedron Lett., 2002, vol. 43, p. 2657.

    Article  CAS  Google Scholar 

  21. Rani, V.R., Srinias, N., Kishan, M.R., Kulkarni, S.J., and Raghavan, K., Green Chem., 2001, vol. 3, p. 305.

    Article  CAS  Google Scholar 

  22. Tayebee, R., Maleki, B., and Ghadamgahi, M., Chin. J. Catal., 2012, vol. 33, p. 659.

    Article  CAS  Google Scholar 

  23. Bose, D.S., Fatima, L., and Mereyala, H.B., J. Org. Chem., 2003, vol. 68, p. 587.

    Article  CAS  Google Scholar 

  24. Wang, D.-C., Guo, H.-M., and Qu, G.-R., Synth. Commun., 2010, vol. 40, p. 1115.

    Article  CAS  Google Scholar 

  25. Mondal, J., Sen, T., and Bhaumik, A., Dalton Trans., 2012, vol. 41, p. 6173.

    Article  CAS  Google Scholar 

  26. Rahmatpour, A., Catal. Lett., 2012, vol. 142, p. 1505.

    Article  CAS  Google Scholar 

  27. Yadav, J.S., Subba Reddy, B.V., Jagan Reddy, E., and Ramalingam, T., J. Chem. Res., Synop., 2000, p. 354

    Google Scholar 

  28. Gupta, R., Gupta, A.K., Paul, S., and Kachroo, P.L., Indian J. Chem., Sect. B, 1995, vol. 34, p. 151

    Google Scholar 

  29. Saxena, I., Borah, D.C., and Sarma, J.C., Tetrahedron Lett., 2005, vol. 46, p. 1159

    Article  CAS  Google Scholar 

  30. Vijayakumar, B. and Rao, G.R., J. Porous Mater., 2012, vol. 19, p. 491.

    Article  CAS  Google Scholar 

  31. Mandhane, P.G., Joshi, R.S., Nagargoje, D.R., and Gill, C.H., Tetrahedron Lett., 2010, vol. 51, p. 3138

    Article  CAS  Google Scholar 

  32. Yadav, J.S., Reddy, K.B., Reddy, B.V.S., Raj, K.S., and Prasad, A.R., J. Chem. Soc., Perkin Trans. 1, 2001, p. 1939.

    Google Scholar 

  33. Zheng, R., Wang, X., Xu, H., and Du, J., Synth. Commun., 2006, vol. 36, p. 1503

    Article  CAS  Google Scholar 

  34. Legeay, J.-C., Eynde, J.J.V., and Bazureau, J.P., Tetrahedron, 2005, vol. 61, p. 12 386

    Article  Google Scholar 

  35. Gholap, A.R., Venkatesan, K., Daniel, T., Lahoti, R.J., and Srinivasan, K.V., Green Chem., 2004, vol. 6, p. 147

    Article  CAS  Google Scholar 

  36. Karthikeyan, P., Aswar, S.A., Muskawar, P.N., Bhagat, P.R., and Kumar, S., J. Organomet. Chem., 2013, vol. 723, p. 154

    Article  CAS  Google Scholar 

  37. Chen, X. and Peng, Y., Catal. Lett., 2008, vol. 122, p. 310.

    Article  CAS  Google Scholar 

  38. Fazaeli, R., Tangestaninejad, S., Aliyan, H., and Moghadam, M., Appl. Catal. A, 2006, vol. 309, p. 44

    Article  CAS  Google Scholar 

  39. Heravi, M.M., Derikvand, F., and Bamoharram, F.F., J. Mol. Catal. A: Chem., 2005, vol. 242, p. 173

    Article  CAS  Google Scholar 

  40. Maradur, S.P. and Gokavi, G.S., Catal. Commun., 2007, vol. 8, p. 279

    Article  CAS  Google Scholar 

  41. Zumpe, F.L., Flub, M., Schmitz, K., and Lender, A., Tetrahedron Lett., 2007, vol. 48, p. 1421.

    Article  CAS  Google Scholar 

  42. Shutalev, A.D., Kishko, E.A., Sivova, N.V., and Kuznetsov, A.Y., Molecules, 1998, vol. 3, p. 100

    Article  CAS  Google Scholar 

  43. Debache, A., Amimour, M., Belfaitah, A., Rhouati, S., and Carboni, B., Tetrahedron Lett., 2008, vol. 49, p. 6119.

    Article  CAS  Google Scholar 

  44. Khodaei, M.M., Khosropour, A.R., and Beygzadeh, M., Synth. Commun., 2004, vol. 34, p. 1551.

    Article  CAS  Google Scholar 

  45. Shaterian, H.R., Hosseinian, A., and Ghashang, M., Phosphorus, Sulfur Silicon Relat. Elem., 2009, vol. 184, p. 197.

    Article  CAS  Google Scholar 

  46. Kefayati, H., Asghari, F., and Khanjanian, R., J. Mol. Liq., 2012, vol. 172, p. 147.

    Article  CAS  Google Scholar 

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Correspondence to M. Hajjami.

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Hajjami, M., Ghiasbeygi, E. First catalyst- and solvent-free synthesis of 3,4-dihydropyrimidin-2(1H)-ones and -thiones. Russ J Org Chem 52, 429–432 (2016). https://doi.org/10.1134/S1070428016030222

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  • DOI: https://doi.org/10.1134/S1070428016030222

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