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CeCl3-promoted one-pot synthesis of multisubstituted bispyrano[2,3-c]pyrazole derivatives

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Abstract

A simple and efficient method was developed for the synthesis of multisubstituted bispyrano[2,3-c]pyrazole derivatives via one-pot reaction of β-keto esters, hydrazine (or phenylhydrazine), terephthalaldehyde, and malononitrile in the presence of CeCl3·7H2O (10 mol%) as a catalyst. This method provides the products in good yields after a simple workup procedure without further purification.

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References

  1. Ough M, Lewis A, Bey EA, Gao J, Ritchie JM, Bornmann W, Boothman DA, Oberley LW, Cullen JJ (2005) Canc Biol Ther 4:95

    Article  CAS  Google Scholar 

  2. Kuo SC, Huang LJ, Nakamura H (1984) J Med Chem 27:539

    Article  CAS  Google Scholar 

  3. Mandha SR, Siliveri S, Alla M, Bommena VR, Bommineni MR, Balasubramanian S (2012) Bioorg Med Chem Lett 22:5272

    Article  CAS  Google Scholar 

  4. Johns BA, Gudmundsson KS, Turner EM, Allen SH, Jung DK, Sexton CJ, Boyd FLJ, Peel MR (2003) Tetrahedron 59:9001

    Article  CAS  Google Scholar 

  5. Abdelrazek FM, Metz P, Metwally NH, El-Mahrouky SF (2006) Arch Pharm 339:456

    Article  CAS  Google Scholar 

  6. Abdelrazek FM, Metz P, Kataeva O, Jaeger A, El-Mahrouky SF (2007) Arch Pharm 340:543

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  8. Devi I, Kumar BSD, Bhuyan PJ (2003) Tetrahedron Lett 44:8307

    Article  CAS  Google Scholar 

  9. Salama TA, Elmorsy SS, Khalil AM, Ismail MA (2007) Tetrahedron Lett 48:6199

    Article  CAS  Google Scholar 

  10. Dömling A (2006) Chem Rev 106:17

    Article  Google Scholar 

  11. Dömling A, Ugi I (2000) Angew Chem Int Ed 39:3168

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

  13. Zhu J, Bienaymé H (2005) Multicomponent reactions. Wiley-VCH, Weinheim

    Book  Google Scholar 

  14. Nagarajan AS, Reddy BS (2009) Synlett 12:2002

    Google Scholar 

  15. Yi H, Song L, Wang W, Liu J, Zhu S, Deng H, Shao M (2010) Chem Commun 46:6941

    Article  CAS  Google Scholar 

  16. Kanagaraj K, Pitchumani K (2010) Tetrahedron Lett 51:3312

    Article  CAS  Google Scholar 

  17. Liu J, Li J, Zhang L, Song L, Zhang M, Cao W, Shao M (2012) Tetrahedron Lett 53:2469

    Article  CAS  Google Scholar 

  18. Shestopalov AM, Emeliyanova YM, Shestopalov AA, Rodinovskaya LA, Niazimbetova ZI, Evans DH (2003) Tetrahedron 59:7491

    Article  CAS  Google Scholar 

  19. Vasuki G, Kumaravel K (2008) Tetrahedron Lett 49:5636

    Article  CAS  Google Scholar 

  20. Ablajan K, Maimaiti Z (2012) Synth Commun 42:1959

    Article  CAS  Google Scholar 

  21. Mecadon H, Rohman MR, Rajbangshi M, Myrboh B (2011) Tetrahedron Lett 52:2523

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  23. Siddekha A, Nizam A, Pasha MA (2011) Spectrochim Acta A Mol Biomol Spectrosc 81:431

    Article  CAS  Google Scholar 

  24. Liu X, Xu X, Wang X, Yang W, Qian Q, Zhang M, Song L, Deng H, Shao M (2013) Tetrahedron Lett 33:4451

    Article  Google Scholar 

  25. Imamoto T (1994) Lanthanides in organic synthesis. Academic, New York

    Google Scholar 

  26. Bartoli G, Bellucci MC, Alessandrini S, Malavolta M, Marcantoni E, Sambri L, Dalpozzo R (1999) J Org Chem 64:1986

    Article  Google Scholar 

  27. Ballini R, Marcantoni E, Perella S (1999) J Org Chem 64:2954

    Article  CAS  Google Scholar 

  28. Bartoli G, Bellucci MC, Petrini M, Marcantoni E, Sambri L, Torregiani E (2000) Org Lett 2:1791

    Article  CAS  Google Scholar 

  29. Sabitha G, Babu RS, Rajkumar M, Srividia R, Yadav JS (2001) Org Lett 3:1149

    Article  CAS  Google Scholar 

  30. Jafari AA, Nazarpour M, Abdollahi-Alibeik M (2010) Heteroatom Chem 21:397

    Article  CAS  Google Scholar 

  31. Sabitha G, Arundhathi K, Sudhakar K, Sastry BS, Yadav JS (2009) Synth Commun 39:433

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We gratefully acknowledge the Natural Science Foundation of China (No. 21162028) and the Natural Science Foundation of Xinjiang Science Technology Agency (No. 2009 211A02).

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Authors and Affiliations

  1. Key Laboratory of Oil and Gas Fine Chemicals, Ministry of Education and Xinjiang Uyghur Autonomous Region, College of Chemistry and Chemical Engineering, Xinjiang University, Urumqi, China

    Keyume Ablajan, Li-Ju Wang, Zulipiya Maimaiti & Yong-Ting Lu

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  1. Keyume Ablajan
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  2. Li-Ju Wang
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  3. Zulipiya Maimaiti
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  4. Yong-Ting Lu
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Correspondence to Keyume Ablajan.

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Ablajan, K., Wang, LJ., Maimaiti, Z. et al. CeCl3-promoted one-pot synthesis of multisubstituted bispyrano[2,3-c]pyrazole derivatives. Monatsh Chem 145, 491–496 (2014). https://doi.org/10.1007/s00706-013-1104-6

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  • DOI: https://doi.org/10.1007/s00706-013-1104-6

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