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α-Zirconium Sulfophenylphosphonate as a Catalyst for the Synthesis of 3,4-Dihydropyrimidin-2(1H)-One Derivatives Under Solvent Free Conditions

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Abstract

3,4-Dihydropyrimidin-2(1H)-one derivatives were synthesized using layered α-zirconium sulfophenylphosphonate as a recyclable heterogeneous catalyst. Several classes of reagents, such as functionalized aromatic and aliphatic aldehydes, β-dicarbonyl derivatives and 2-aminobenzimidazole, were used to synthesize different 3,4-dihydropyrimidin-2(1H)-one derivatives under solvent free conditions.

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References

  1. Curini M, Rosati O, Costantino U (2004) Cur Org Chem 8:591

    Article  CAS  Google Scholar 

  2. Alberti G, Casciola M, Costantino U, Vivani R (1996) Adv Mater 8:291

    Article  CAS  Google Scholar 

  3. Costantino U, Curini M, Rosati O, Pisani E (1996) Synlett 333–334

  4. Costantino U, Curini M, Marcotullio MC, Pisani E, Rosati O (1997) Synlett 769–770

  5. Curini M, Epifano F, Marcotullio MC, Rosati O, Costantino U (1998) Tetrahedron Lett 39:8159

    Article  CAS  Google Scholar 

  6. Curini M, Epifano F, Marcotullio MC, Rosati O, Costantino U (1999) Synt Commun 29:541

    Article  CAS  Google Scholar 

  7. Curini M, Epifano F, Marcotullio MC, Rosati O (2000) Synt Commun 30:1319

    Article  CAS  Google Scholar 

  8. Curini M, Epifano F, Marcotullio MC, Rosati O (2001) Synlett 7:1182

    Article  Google Scholar 

  9. Curini M, Epifano F, Marcotullio MC, Rosati O, Nocchetti M (2002) Tetrahedron Lett 43:2709

    Article  CAS  Google Scholar 

  10. Curini M, Epifano F, Marcotullio MC, Rosati O (2001) Eur J Org Chem 21:4149

    Article  Google Scholar 

  11. Curini M, Montanari F, Rosati O, Lioy E, Margarità R (2003) Tetrahedron Lett 44:3923

    Article  CAS  Google Scholar 

  12. Curini M, Rosati O, Campagna V, Montanari F, Cravotto G, Boccalini M (2005) Synlett 19:2927

    Article  Google Scholar 

  13. Rosati O, Curini M, Marcotullio MC, Macchiarulo A, Perfumi M, Mattioli L, Rismondo F, Cravotto G (2007) Bioorg Med Chem 15:3463

    Article  CAS  Google Scholar 

  14. Ugi I, Domling A, Horl W (1994) Endeavour 18:115

    Article  CAS  Google Scholar 

  15. Tietze LF, Lieb ME (1998) Curr Opin Chem Biol 2:363

    Article  CAS  Google Scholar 

  16. Mabry J, Ganem B (2006) Tetrahedron Lett 47:55

    Article  CAS  Google Scholar 

  17. Biginelli P (1893) Gazz Chim Ital 23:360

    Google Scholar 

  18. Kolosov MA, Orlov VD, Beloborodov DA, Dotsenko VV (2009) Mol Divers 13:5

    Article  CAS  Google Scholar 

  19. Phucho IT, Nongpiur A, Tumtin S, Nongrum R, Nongkhlaw RL (2009) Rasayan J Chem 2:662

    CAS  Google Scholar 

  20. Kappe CO (2000) Eur J Med Chem 35:1043

    Article  CAS  Google Scholar 

  21. Kappe CO (1998) Molecules 3:1

    Article  CAS  Google Scholar 

  22. Atwal KS, Swanson BN, Unger SE, Floyd DM, Moreland S, Hedberg A, O’Reilly BC (1991) J Med. Chem 34:806

    CAS  Google Scholar 

  23. Grover GJ, Dzwonczyk S, Mc Mullen DM, Normadinam CS, Sleph PG, Moreland SJ J (1995) Cardiovasc Pharmacol 26:289

    Article  CAS  Google Scholar 

  24. Kappe CO (2000) Acc Chem Res 33:879

    Article  CAS  Google Scholar 

  25. Klein E, De Bonis S, Thiede B, Skoufias DA, Kozielski F, Lebeau L (2007) Bioorg Med Chem 15:6474

    Article  CAS  Google Scholar 

  26. Quan ZJ, Da YX, Zhang Z, Wang XC (2009) Catalysis Commun 10:1146

    Article  CAS  Google Scholar 

  27. Tamaddon F, Razmi Z, Jafari AA (2010) Tetrahedron Lett 51:1187

    Article  CAS  Google Scholar 

  28. Gorobets NY, Sedash YV, Ostras KS, Zaremba OV, Shishkina SV, Baumer VN, Shishkin OV, Kovalenko SM, Desenko SM, Van der Eycken EV (2010) Tetrahedron Lett 51:2095–2098

    Article  CAS  Google Scholar 

  29. Zhang H, Zhou Z, Yao Z, Xu F, Shen Q (2009) Tetrahedron Lett 50:1622

    Article  CAS  Google Scholar 

  30. Chandak HS, Lad NP, Upare PP (2009) Catal Lett 131:469

    Article  CAS  Google Scholar 

  31. Ah BJ, Gang MS, Chae K, Oh Y, Shin J, Chang W (2008) J Ind Eng Chem 14:401

    Google Scholar 

  32. Singh K, Arora D, Singh S (2006) Tetrahedron Lett 47:4205

    Article  CAS  Google Scholar 

  33. Anastas PT, Warner JC (1998) Green chemistry: theory and pratctice. Oxford University Press, New York

    Google Scholar 

  34. Metzger JO (1997) Angew Chem Int Ed 36:783

    Article  CAS  Google Scholar 

  35. Corma A (1997) Chem Rev 97:2373

    Article  CAS  Google Scholar 

  36. Clark JH, Macquarrie D (1996) J Chem Soc Rev 25:303

    Article  CAS  Google Scholar 

  37. Bellezza F, Cipiciani A, CostantinoU Fringuelli F, Orrù M, Piermatti O, Pizzo F (2010) Catal Today 152:61

    Article  CAS  Google Scholar 

  38. Fringuelli F, Lanari D, Pizzo F, Vaccaro (2010) Green Chem 12:1301

    Article  CAS  Google Scholar 

  39. Prashantha Kumar BR, Masih P, Karthikeyan E, Bansal A, Suja Vijayan P (2010) Med Chem Res 19:344

    Article  CAS  Google Scholar 

  40. Prokopcová H, Pisani L, Kappe CO (2007) Synlett 13:43

    Google Scholar 

  41. Yao CS, Lei S, Wang CH, Yu CX, Shao QQ, Tu SJ (2008) Chinese J Chem 26:2107

    Article  CAS  Google Scholar 

  42. Salehi H, Li Q, Guo Q (2006) Chin J Chem Phys 19:84

    Article  CAS  Google Scholar 

  43. Kumar A, Maurya RA (2007) Tetrahedron Lett 48:4569

    Article  CAS  Google Scholar 

  44. Singh K, Arora D, Falkowski D, Liu Q, Moreland RS (2009) Eur J Org Chem 3258–3264

Download references

Acknowledgment

Financial support from MIUR, National Project 2008 “Approccio ecocompatibile all’intensificazione di processo nella sintesi organica” is gratefully acknowledged.

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Correspondence to Ornelio Rosati.

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Rosati, O., Curini, M., Montanari, F. et al. α-Zirconium Sulfophenylphosphonate as a Catalyst for the Synthesis of 3,4-Dihydropyrimidin-2(1H)-One Derivatives Under Solvent Free Conditions. Catal Lett 141, 850–853 (2011). https://doi.org/10.1007/s10562-011-0604-4

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