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A facile access to 1,3,4-trisubstituted pyrazoles via 1,3-dipolar cycloaddition of 3-arylsydnones with α,β-unsaturated ketones

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Abstract

A novel one-pot synthesis of 1,3,4-trisubstituted pyrazoles has been accomplished by 1,3-dipolar cycloaddition of α,β-unsaturated ketones and 3-arylsydnones in dry xylene. The structural identities of these compounds were confirmed on the basis of IR, NMR, mass spectral, and X-ray analysis.

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References

  1. Gomez L, Hack MD, Wu J, Wiener JJM, Venkatesan HAS, Pippel DJ, Mani N, Morrow BJ, Motley ST, Shaw KJ, Wolin R, Grice CA, Jones TK (2007) Bioorg Med Chem Lett 17:2723

    Article  CAS  Google Scholar 

  2. Regan J, Breitfelder S, Cirillo P, Gilmore T, Graham AG, Hickey E, Klaus B, Madwed J, Moriak M, Moss N, Pargellis C, Pav S, Proto A, Swinamer A, Tong L, Torcellini C (2002) J Med Chem 45:2994

    Article  CAS  Google Scholar 

  3. Pinto DJP, Orwat MJ, Koch S, Rossi KA, Alexander RS, Smallwood A, Wong PC, Rendina AR, Luettgen JM, Knabb RM, He K, Xin B, Wexler RR, Lam PYS (2007) J Med Chem 50:5339

    Article  CAS  Google Scholar 

  4. Ghotekar BK, Ghagare MG, Toche RB, Jachak MN (2010) Monatsh Chem 141:169

    Article  CAS  Google Scholar 

  5. Chimenti F, Bolasco A, Manna F, Secci D, Chimenti P, Granese A, Befani O, Turini P, Alcaro S, Ortuso F (2006) Chem Biol Drug Des 67:206

    Article  CAS  Google Scholar 

  6. Lin R, Chiu G, Yu Y, Connolly PJ, Li SJ, Lu YH, Adams M, Fuentes-Pesquera AR, Emanuel SL, Greenberger LM (2007) Bioorg Med Chem Lett 17:4557

    Article  CAS  Google Scholar 

  7. Penning TD, Talley JJ, Bertenshaw SR, Carter JS, Collins PW, Docter S, Graneto MJ, Lee LF, Malecha JW, Miyashiro JM, Rogers RS, Rogier DJ, Yu SS, Anderson GD, Burton EG, Cogburn JN, Gregory SA, Koboldt CM, Perkins WE, Seibert K, Veenhuizen AW, Zhang YY, Isakson PC (1997) J Med Chem 40:1347

    Article  CAS  Google Scholar 

  8. Elguero J, Goya P, Jagerovic N, Silva AMS (2002) In: Attanasi OA, Spinelli D (eds) Targets in heterocyclic systems—chemistry and properties, vol 6. Italian Society of Chemistry, Rome, p 52

    Google Scholar 

  9. Fustero S, Sánchez-Roselló M, Barrio P, Simón-Fuentes A (2011) Chem Rev 111:6984

    Article  CAS  Google Scholar 

  10. Martins MAP, Peres RL, Frizzo CP, Scapin E, Moreira DN, Fiss GF, Zanatta N, Bonacorso HG (2009) J Heterocycl Chem 46:1247

    Article  CAS  Google Scholar 

  11. Reidlinger C, Dworczak R, Junek H (1998) Monatsh Chem 129:1207

    CAS  Google Scholar 

  12. Silva VLM, Silva AMS, Pinto DCGA, Jagerovic N, Callado LF, Cavaleiro JAS, Elguero J (2007) Monatsh Chem 138:797

    Article  CAS  Google Scholar 

  13. Chimenti F, Bolasco A, Manna F, Secci D, Chimenti P, Granese A, Befani O, Turini P, Alcaro S, Ortuso F (2006) Chem Biol Drug Des 67:206

    Article  CAS  Google Scholar 

  14. Nikpour F, Beigvand M (2008) Monatsh Chem 139:821

    Article  CAS  Google Scholar 

  15. Makino K, Kim HS, Kurasawa Y (1998) J Heterocycl Chem 35:489

    Article  CAS  Google Scholar 

  16. Hegde JC, Rai G, Puranik VG, Kalluraya B (2006) Synth Commun 36:1285

    Article  CAS  Google Scholar 

  17. Rai NS, Balakrishna Kalluraya B, Lingappa B, Shaliny Shenoy S, Puranic VG (2008) Eur J Med Chem 43:1715

    Article  Google Scholar 

  18. Al-Shiekh MA (2005) Org Prep Proced Int 37:223

    Article  CAS  Google Scholar 

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Acknowledgments

We are grateful to the Key SCI-Tech Innovation Team of Zhejiang Province (2010R5 0017) for financial help.

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Correspondence to Fei Chen.

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Chen, F., Liu, FM., Shi, H. et al. A facile access to 1,3,4-trisubstituted pyrazoles via 1,3-dipolar cycloaddition of 3-arylsydnones with α,β-unsaturated ketones. Monatsh Chem 144, 879–884 (2013). https://doi.org/10.1007/s00706-012-0901-7

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  • DOI: https://doi.org/10.1007/s00706-012-0901-7

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