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TSA-catalyzed regioselective synthesis of medicinally important 4-aryl-substituted dihydropyrimidine derivatives fused to pyrazole and triazole scaffolds via an efficient and green Domino reaction

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Abstract

A novel class of medicinally important 4-aryl-substituted dihydropyrimidine derivatives fused to pyrazole and triazole scaffolds has been found which is obtained via a newly designed regioselective domino reaction using tungstate sulfuric acid (TSA) as a Brønsted acid recyclable catalyst. Throughout this tri-component tandem reaction, 4-aryl-substituted dihydropyrimidine derivatives fused to pyrazole and triazole moieties were regioselectively formed under environmentally benign solvent-free conditions with high yields. By this achievement, some novel potentially interesting biologically active products were synthesized via a green and eco-friendly procedure.

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References

  1. Dömling A, Ugi IA (2000) Angew Chem Int Ed 39:3168

    Article  Google Scholar 

  2. Dömling A, Wang W, Wang K (2012) Chem Rev 112:3083

    Article  Google Scholar 

  3. Rotstein BH, Zaretsky S, Rai V, Yudin AK (2014) Chem Rev 114:8323

    Article  CAS  Google Scholar 

  4. Tamaddon F, Farahi M, Karami B (2011) J Mol Catal A Chem 337:52

    Article  CAS  Google Scholar 

  5. Eskandari K, Karami B, Khodabakhshi S (2014) J Chem Res 38:600

    Article  CAS  Google Scholar 

  6. Eskandari K, Karami B, Khodabakhshi S, Farahi M (2015) Lett Org Chem 12:38

    Article  CAS  Google Scholar 

  7. Liao WL, Li SQ, Wang J, Zhang ZY, Yang ZW, Xu D, Xu C, Lan HT, Chen ZZ, Xu ZG (2016) ACS Comb Sci 18:65

    Article  CAS  Google Scholar 

  8. Eskandari K, Karami B (2016) Monatsh Chem 147:2119

    Article  CAS  Google Scholar 

  9. De Coen LM, Heugebaert TSA, Garcia D, Stevens CV (2016) Chem Rev 116:80

    Article  Google Scholar 

  10. Kralisch D, Ott D, Gericke D (2015) Green Chem 17:123

    Article  CAS  Google Scholar 

  11. Wenda S, Illner S, Mell A, Kragl U (2011) Green Chem 13:3007

    Article  CAS  Google Scholar 

  12. Singh MS, Chowdhury S (2012) RSC Adv 2:4547

    Article  CAS  Google Scholar 

  13. Karami B, Farahi M, Pam F (2014) Tetrahedron Lett 55:6292

    Article  CAS  Google Scholar 

  14. Ralphs K, Hardacre C, James SL (2013) Chem Soc Rev 42:7701

    Article  CAS  Google Scholar 

  15. Feng J, He Y, Liu Y, Dua Y, Li D (2015) Chem Soc Rev 44:5291

    Article  CAS  Google Scholar 

  16. Karami B, Eskandari K, Gholipour S, Jamshidi M (2013) Org Prep Proced Int 45:220

    Article  CAS  Google Scholar 

  17. Karami B, Farahi M, Banaki Z (2015) Synlett 26:1804

    Article  CAS  Google Scholar 

  18. Khodabakhshi S, Karami B, Eskandari K, Farahi M (2014) Tetrahedron Lett 55:3753

    Article  CAS  Google Scholar 

  19. Poorali L, Karami B, Eskandari K, Azizi M (2013) J Chem Sci 125:591

    Article  CAS  Google Scholar 

  20. Kantam ML, Roy M, Roy S, Sreedhar B, Lal-De R (2008) Catal Commun 9:2226

    Article  CAS  Google Scholar 

  21. Murkute AD, Jackson JE, Miller DJ (2011) J Catal 278:189

    Article  CAS  Google Scholar 

  22. Karami B, Eskandari K, Azizi M (2013) Lett Org Chem 10:722

    Article  CAS  Google Scholar 

  23. Farahi M, Karami B, Sedighimehr I, Mohamadi-Tanuraghaj H (2014) Chin Chem Lett 25:1580

    Article  CAS  Google Scholar 

  24. Farahi M, Karami B, Azari M (2013) C R Chim 16:1029

    Article  CAS  Google Scholar 

  25. Goel N, Drabu S, Afzal O, Bawa S (2014) J Pharm BioAllied Sci 6:253

    Article  CAS  Google Scholar 

  26. Bender CM, Merriman JD, Gentry AL, Ahrendt GM, Berga SL, Brufsky AM, Casillo FE, Dailey MM, Erickson KI, Kratofil FM, McAuliffe PF, Rosenzweig MQ, Ryan CM, Sereika SM (2015) Cancer 121:2627

    Article  CAS  Google Scholar 

  27. Hertz DL, Barlow WE, Kidwell KM, Albain KS, Vandenberg TA, Dakhil SR, Tirumali NR, Livingston RB, Gralow J, Hayes DF, Hortobagyi GN, Mehta RS, Rae JM (2016) Br J Clin Pharmacol 81:1134

    Article  CAS  Google Scholar 

  28. Da Silva AR, De Andrade-Neto JB, Da Silva CR, Campos-Rde S, Costa-Silva RA, Freitas DD, Nascimento DFB, De Andrade LN, Sampaio LS, Grangeiro TB, Magalhaes HI, Cavalcanti BC, De Moraes MO, Nobre-Junior HV (2016) Antimicrob Agents Chemother 60:3551

    Article  Google Scholar 

  29. Cikla-Süzgün P, Kaushik-Basu N, Basu A, Arora P, Talele TT, Durmaz I, Cetin-Atalay R, Kücükgüzel SG (2015) J Enzyme Inhib Med Chem 30:778

    Article  Google Scholar 

  30. Purohit MN, Panjamurthy K, Elango S, Hebbar K, Mayur YC, Raghavan SC (2011) Nucleosides. Nucleotides Nucleic Acids 30:873

    Article  CAS  Google Scholar 

  31. Patel NB, Khan IH (2011) J Enzyme Inhib Med Chem 26:527

    Article  CAS  Google Scholar 

  32. Plech T, Wujec M, Kosikowska U, Malm A, Rajtar B, Polz-Dacewicz M (2013) Eur J Med Chem 60:128

    Article  CAS  Google Scholar 

  33. Somorai T, Szilagyi G, Reiter J, Pongo L, Lang T, Toldy L, Horvath S (1986) Arch Pharm 319:238

    Article  CAS  Google Scholar 

  34. Kaplancikli ZA, Turan-Zitouni G, Ozdemir A, Revail G (2008) Eur J Med Chem 43:155

    Article  CAS  Google Scholar 

  35. El-Shehry MF, Abu-Hashem AA, El-Telbani EM (2010) Eur J Med Chem 45:1906

    Article  CAS  Google Scholar 

  36. Chen J, Sun XY, Chai KY, Lee JS, Song MS, Quan ZS (2007) Bioorg Med Chem 15:6775

    Article  CAS  Google Scholar 

  37. Almajan GL, Barbucenau SF, Almajan ER, Draghici C, Saramet G (2009) Eur J Med Chem 44:3083

    Article  CAS  Google Scholar 

  38. Kolos NN, Kovalenko LU, Borovskoy VA (2011) Chem Heterocycl Compd 47:983

    Article  CAS  Google Scholar 

  39. Ruisi G, Canfora L, Bruno G, Rotondo A, Mastropietro TF, Debbia EA, Girasolo MA, Megna B (2010) J Organomet Chem 695:546

    Article  CAS  Google Scholar 

  40. El-Gendy MMA, Shaaban M, Shaaban KA, El-Bondkly AM, Laatsch H (2008) J Antibiot 61:149

    Article  CAS  Google Scholar 

  41. Blunt JW, Copp BR, Munro MHG, Northcote PT, Prinsep MR (2010) Nat Prod Rep 27:165

    Article  CAS  Google Scholar 

  42. Rudenko RV, Komykhov SA, Musatov VI, Desenko SM (2009) J Heterocycl Chem 46:285

    Article  CAS  Google Scholar 

  43. Magan R, Marin C, Rosales MJ, Salas JM (2005) Pharmacology 73:41

    Article  CAS  Google Scholar 

  44. Dandia A, Sarawgi P, Arya K, Khanturia S (2006) Arkivoc XVI:83

    Google Scholar 

  45. Farahi M, Davoodi M, Tahmasebi M (2016) Tetrahedron Lett 57:1582

    Article  CAS  Google Scholar 

  46. Eskandari K, Karami B, Farahi M, Mouzari V (2016) Tetrahedron Lett 57:487

    Article  CAS  Google Scholar 

  47. Karami B, Eskandari K, Farahi M, Barmas A (2012) J Chin Chem Soc 59:473

    Article  CAS  Google Scholar 

  48. Tamaddon F, Farahi M (2012) Synlett 23:1379

    Article  CAS  Google Scholar 

  49. Ma N, Jiang B, Zhang GE, Tu SJ, Wever W, Li G (2010) Green Chem 12:1357

    Article  CAS  Google Scholar 

  50. Ramalingan C, Park SJ, Lee IS, Kwak YW (2010) Tetrahedron 66:2987

    Article  CAS  Google Scholar 

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Acknowledgements

The authors would like to gratefully thank Yasouj University Research Council for partial support of this work.

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Authors and Affiliations

  1. Department of Chemistry, Yasouj University, P. O. Box 353, Yasouj, 75918-74831, Iran

    Mahnaz Farahi, Bahador Karami, Zohreh Banaki & Fatemeh Rastgoo

  2. Young Researchers and Elites ClubShahrekord Branch, Islamic Azad University, Shahrekord, Iran

    Khalil Eskandari

Authors
  1. Mahnaz Farahi
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  2. Bahador Karami
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  3. Zohreh Banaki
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  4. Fatemeh Rastgoo
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  5. Khalil Eskandari
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Corresponding authors

Correspondence to Mahnaz Farahi or Khalil Eskandari.

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Farahi, M., Karami, B., Banaki, Z. et al. TSA-catalyzed regioselective synthesis of medicinally important 4-aryl-substituted dihydropyrimidine derivatives fused to pyrazole and triazole scaffolds via an efficient and green Domino reaction. Monatsh Chem 148, 1469–1475 (2017). https://doi.org/10.1007/s00706-017-1932-x

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  • DOI: https://doi.org/10.1007/s00706-017-1932-x

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