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Solvent-free and ‘on-water’ multicomponent assembling of aldehydes, 3-methyl-2-pyrazoline-5-one, and malononitrile: fast and efficient approach to medicinally relevant pyrano[2,3-c]pyrazole scaffold

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Abstract

Sodium acetate-catalyzed multicomponent reaction of aldehydes, 3-methyl-2-pyrazoline-5-one, and malononitrile initiated by grinding in mortar in the presence of small quantities of water results in the fast (15 min) and efficient formation of substituted pyrano[2,3-c]pyrazoles in 90–95 % yields. The developed fast multicomponent approach to the substituted pyrano[2,3-c]pyrazoles—the known pharmacologically active substances such as antibiotics, enzyme inhibitors, and anticancer drugs––is beneficial from the viewpoint of diversity-oriented large-scale processes and represents fast efficient and environmentally benign synthetic concept for multicomponent reactions strategy.

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References

  1. Corma A, Garcia H (2003) Chem Rev 103:4307

    Article  CAS  Google Scholar 

  2. Sheldon RA (2000) Pure Appl Chem 72:1233

    Article  CAS  Google Scholar 

  3. Evans BE, Rittle KE, Bock G, DiPardo RM, Freidinger FM, Whitter WL, Lundell GF, Veber DF, Anderson PS, Chang RSL, Lotti VG, Cerino DJ, Chen TB, Kling PJ, Kunkel KA, Springer JP, Hirshfield J (1988) J Med Chem 31:2235

    Article  CAS  Google Scholar 

  4. Poupaert O, Carato P, Colacino E (2005) Curr Med Chem 12:877

    Article  CAS  Google Scholar 

  5. Song Y, Zhan P, Zhang QZ, Liu XY (2013) Curr Pharm Design 19:1528

    CAS  Google Scholar 

  6. Mishriky N, Girgis AS, Asaad FM, Ibrahim YA, Sobieh UI, Fawzy NG (2001) Boll Chim Farm 140:129

    CAS  Google Scholar 

  7. Coen DM, Loregian A (2006) Antiviral methods and compositions. International Patent WO 2006019955, Feb 23, 2006

  8. Coen DM, Loregian A (2007) Chem Abstr 147:398624

    Google Scholar 

  9. Foloppe N, Fisher LM, Howes R, Potter A, Robertson AGS, Surgenor AE (2006) Bioorg Med Chem 14:4792

    Article  CAS  Google Scholar 

  10. Kaiser D, Terfloth L, Kopp S, Schulz J, de Laet R, Chiba P, Ecker GF, Gasteiger J (2007) J Med Chem 50:1698

    Article  CAS  Google Scholar 

  11. La Motta C, Sartini S, Tuccinardi T, Nerini E, Da Settimo F, Martinelli A (2009) J Med Chem 52:964

    Article  Google Scholar 

  12. Abdou S, Fahmy SM, Sadek KU, Elnagdi MH (1981) Heterocycles 16:177

    Article  Google Scholar 

  13. Elnagdi MH, Abdel-Motaleb RM, Mustafa M, Zayed MF, Kamel EM (1987) J Heterocycl Chem 24:1677

    Article  CAS  Google Scholar 

  14. Abdel-Latif FF (1990) Z Naturforsch B 45:1675

    Article  CAS  Google Scholar 

  15. Sharanin YA, Sharanina LG, Puzanova VV (1983) J Org Chem USSR 19:2291

    Google Scholar 

  16. Sheibani H, Babaie M (2010) Synth Commun 40:257

    Article  CAS  Google Scholar 

  17. Shanthi G, Subbulakshmi G, Perumal PT (2007) Tetrahedron 63:2057

    Article  CAS  Google Scholar 

  18. Heravi MM, Ghods A, Derikvand F, Bakhtiari K, Bamoharram FF (2010) J Iran Chem Soc 7:615

    Article  CAS  Google Scholar 

  19. Dandia A, Jain AK, Bhati DS (2011) Synth Commun 41:2905

    Article  CAS  Google Scholar 

  20. Zhou JF, Tu SJ, Zhu HQ, Zhi SJ (2002) Synth Commun 32:3363

    Article  CAS  Google Scholar 

  21. Thakur A, Tripathi M, Rajesh UC, Rawat DS (2013) RCS Advances 3:18142

    CAS  Google Scholar 

  22. Al-Matar HM, Khalil KD, Adam AY, Elnagdi MH (2010) Molecules 15:6619

    Article  CAS  Google Scholar 

  23. Mecadon H, Rohman MR, Kharbangar I, Laloo BM, Kharkongor I, Rajbangshi M, Myrboh B (2011) Tetrahedron Lett 52:3228

    Article  CAS  Google Scholar 

  24. Kshirsagar SW, Patil NR, Samant SD (2011) Synth Commun 41:1320

    Article  CAS  Google Scholar 

  25. Darandale SN, Sangshetti JN, Shinde DB (2012) J Korean Chem Soc 56:328

    Article  CAS  Google Scholar 

  26. Elinson MN, Medvedev MG, Ilovaisky AI, Merkulova VM, Zaimovskaya TA, Nikishin GI (2013) Mendeleev Commun 23:94

    Article  CAS  Google Scholar 

  27. Elinson MN, Nasybullin RF, Ryzhkov FV, Zaimovskaya TA, Egorov MP (2014) Monatsh Chem 145:605

    Article  CAS  Google Scholar 

  28. Elinson MN, Ilovaisky AI, Merkulova VM, Chizhov AO, Belyakov PA, Nikishin GI (2010) Tetrahedron 66:4043

    Article  CAS  Google Scholar 

  29. Demchuk DV, Elinson MN, Nikishin GI (2011) Mendeleev Commun 21:224

    Article  CAS  Google Scholar 

  30. Patai S, Israeli Y (1960) J Chem Soc: 2025

  31. Lindström NM (ed) (2007) Organic reactions in water: principles, strategies and application. Blackwell, New York

    Google Scholar 

  32. Narayan S, Muldoon J, Finn MJ, Fokin VV, Kolb HC, Sharpless KB (2005) Angew Chem Int Ed 44:3275

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors gratefully acknowledge the financial support of the Russian Foundation for Basic Research (Project No. 13-03-00096a).

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Authors and Affiliations

  1. N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation

    Michail N. Elinson, Ruslan F. Nasybullin, Fedor V. Ryzhkov & Gennady I. Nikishin

  2. A. V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, Moscow, Russian Federation

    Tatiana A. Zaimovskaya

Authors
  1. Michail N. Elinson
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  2. Ruslan F. Nasybullin
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  3. Fedor V. Ryzhkov
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  4. Tatiana A. Zaimovskaya
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  5. Gennady I. Nikishin
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Corresponding author

Correspondence to Michail N. Elinson.

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Elinson, M.N., Nasybullin, R.F., Ryzhkov, F.V. et al. Solvent-free and ‘on-water’ multicomponent assembling of aldehydes, 3-methyl-2-pyrazoline-5-one, and malononitrile: fast and efficient approach to medicinally relevant pyrano[2,3-c]pyrazole scaffold. Monatsh Chem 146, 631–635 (2015). https://doi.org/10.1007/s00706-014-1318-2

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  • DOI: https://doi.org/10.1007/s00706-014-1318-2

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