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Multicomponent Synthesis of Dihydropyrano[2,3-c]pyrazoles Catalyzed by Zinc-Proline Complex

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Abstract

An efficient, suitable and high yielding method has been developed for the synthesis of dihydro­pyrano­[2,3-c]pyrazoles via multicomponent one-pot domino reaction of aromatic aldehydes, malononitrile, ethyl acetoacetate, and hydrazine hydrate in the presence of a catalytic amount of zinc–proline complex Zn[L-proline]2. Atom economy, good to excellent yields, operational simplicity, and easy work-up are some of the important features of this method.

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REFERENCES

  1. Strubing, D., Neumann, H., Klaus, S., Hubner, S., and Beller, M., Tetrahedron, 2005, vol. 61, p. 11333. https://doi.org/10.1016/j.tet.2005.09.097

    Article  CAS  Google Scholar 

  2. Davoodnia, A., Heravi, M.M., Rezaei-Daghigh, L., and Tavakoli-Hoseini, N., Monatsh. Chem., 2009, vol. 140, p. 1499. https://doi.org/10.1007/s00706-009-0193-8

    Article  CAS  Google Scholar 

  3. Yu, L., Chen, B., and Huang, X., Tetrahedron Lett., 2007, vol. 48, p. 925. https://doi.org/10.1016/j.tetlet.2006.12.026

    Article  CAS  Google Scholar 

  4. Davoodnia, A., Bakavoli, M., Moloudi, R., Khashi, M., and Tavakoli-Hoseini, N., Monatsh. Chem., 2010, vol. 141, p. 867. https://doi.org/10.1007/s00706-010-0329-x

    Article  CAS  Google Scholar 

  5. Huang, L.J., Hour, M.J., Teng, C.M., and Kuo, S.C., Chem. Pharm. Bull., 1992, vol. 40, p. 2547. https://doi.org/10.1248/cpb.40.2547

    Article  CAS  Google Scholar 

  6. Shaabani, A., Sarvary, A., Rezayan, A.H., and Keshipour, S., Tetrahedron, 2009, vol. 65, p. 3492. https://doi.org/10.1016/j.tet.2009.02.035

    Article  CAS  Google Scholar 

  7. Martínez-Grau, A. and Marco, J., Bioorg. Med. Chem. Lett., 1997, vol. 7, p. 3165. https://doi.org/10.1016/S0960-894X(97)10165-2

    Article  Google Scholar 

  8. Albadi, J., Mansournezhad, A., and Derakhshandeh, Z., Chin. Chem. Lett., 2013, vol. 24, p. 821. https://doi.org/10.1016/j.cclet.2013.05.031

    Article  CAS  Google Scholar 

  9. De Andrade-Neto, V.F., Goulart, M.O.F., and da Silva Filho, J.F., Bioorg. Med. Chem. Lett., 2004, vol. 14, p. 1145. https://doi.org/10.1016/j.bmcl.2003.12.069

    Article  CAS  PubMed  Google Scholar 

  10. Moon, D.O., Kim, K.C., Jin, C.Y., Han, M.H., Park, C., Lee, K.J., Park, Y.M., Choi, Y.H., and Kim, G.Y., Int. Immunopharmacol., 2007, vol. 7, p. 222. https://doi.org/10.1016/j.intimp.2006.10.001

    Article  CAS  PubMed  Google Scholar 

  11. Venkatesham, A., Rao, R.S., Nagaiah, K., Yadav, J.S., RoopaJones, G., Sridhar, B., and Addlagatta, A., Med. Chem. Commun., 2012, vol. 3, p. 652. https://doi.org/10.1039/C2MD20023F

    Article  CAS  Google Scholar 

  12. Rueping, M., Sugiono, V., and Merino, E., Chem. Eur. J., 2008, vol. 14, p. 6329. https://doi.org/10.1002/chem.200800836

    Article  CAS  PubMed  Google Scholar 

  13. Abdelrazek, F.M., Metz, P., Kataeva, O., Jager, A., and El-Mahrouky, S.F., Arch. Pharm., 2007, vol. 340, p. 543. https://doi.org/10.1002/ardp.200700157

    Article  CAS  Google Scholar 

  14. Ismail, Z.H., Aly, G.M., El-Degwi, M.S., Heiba, H.I., and Ghorab, M.M., Egypt. J. Biotechnol., 2003, vol. 13, p. 73.

    CAS  Google Scholar 

  15. Shaterian, H.R. and Azizi, K., Res. Chem. Intermed., 2014, vol. 40, p. 661. https://doi.org/10.1007/s11164-012-0991-1

    Article  CAS  Google Scholar 

  16. Safaei-Ghomi, J., Ziarati, A., and Tamimi, M., Acta. Chim. Slov., 2013, vol. 60, p. 403.

    CAS  PubMed  Google Scholar 

  17. ElAleem, M.A. and El-Remaily, A.A., Tetrahedron, 2014, vol. 70, p. 2971. https://doi.org/10.1016/j.tet.2014.03.024

    Article  CAS  Google Scholar 

  18. Saha, A., Payra, S., and Banerjee, S., RSC Adv., 2015, vol. 5, p. 101664. https://doi.org/10.1039/C5RA19290K

    Article  CAS  Google Scholar 

  19. Paul, S., Bhattacharyya, P., and Das, A.R., Tetrahedron Lett., 2011, vol. 52, p. 4636. https://doi.org/10.1016/j.tetlet.2011.06.101

    Article  CAS  Google Scholar 

  20. Mehrabi, H. and Kazemi-Mireki, M., Chin. Chem. Lett., 2011, vol. 22, p. 1419. https://doi.org/10.1016/j.cclet.2011.06.003

    Article  CAS  Google Scholar 

  21. Zolfigol, M.A., Tavasoli, M., Moosavi-Zare, A.R., Moosavi, P., Kruger, H.G., Shiri, M., and Khaky­zadeh, V., RSC Adv., 2013, vol. 3, p. 25681. https://doi.org/10.1039/C3RA45289A

    Article  CAS  Google Scholar 

  22. Ablajan, K., Liju, W., Kelimu, Y., and Jun, F., Mol. Diversity, 2013, vol. 17, p. 693. https://doi.org/10.1007/s11030-013-9465-7

    Article  CAS  Google Scholar 

  23. Davarpanah, J. and Kiasat, A.R., RSC Adv., 2014, vol. 4, p. 4403. https://doi.org/10.1039/C3RA43443E

    Article  CAS  Google Scholar 

  24. Sarrafi, Y., Mehrasbi, E., Vahid, A., and Tajbakhsh, M., Chin. J. Catal., 2012, vol. 33, p. 1486. https://doi.org/10.1016/S1872-2067(11)60423-3

    Article  CAS  Google Scholar 

  25. Keyume, A., Esmayil, Z., Wang, L., and Jun, F., Tetrahedron, 2014, vol. 70, p. 3976. https://doi.org/10.1016/j.tet.2014.04.088

    Article  CAS  Google Scholar 

  26. Bhavanarushi, S., Kanakaiah, V., Yakaiah, E., Saddanapu, V., Addlagatta, A., and Rani, J.V., Med. Chem. Res., 2013, vol. 22, p. 2446. https://doi.org/10.1007/s00044-012-0239-z

    Article  CAS  Google Scholar 

  27. Khan, A.T., Lal, M., Ali, S., and Khan, M.M., Tetrahedron Lett., 2011, vol. 52, p. 5327. https://doi.org/10.1016/j.tetlet.2011.08.019

    Article  CAS  Google Scholar 

  28. Shaabani, A., Ghadari, R., Ghasemi, S., Pedarpour, M., Rezayan, A.H., Sarvary, A., and Ng, S.W., J. Comb. Chem., 2009, vol. 11, p. 956. https://doi.org/10.1021/cc900101w

    Article  CAS  PubMed  Google Scholar 

  29. Liju, W. and Ablajan, K., Curr. Org. Synth., 2014, vol. 11, p. 310. https://doi.org/10.2174/15701794113106660079

    Article  CAS  Google Scholar 

  30. Rai, P., Srivastava, M., Singh, J., and Singh, J., New J. Chem., 2014, vol. 38, p. 3181. https://doi.org/10.1039/C3NJ01545A

    Article  CAS  Google Scholar 

  31. Gujar, J.B., Chaudhari, M.A., Kawade, D.S., and Shingare, M.S., Tetrahedron Lett., 2014, vol. 55, p. 6030. https://doi.org/10.1016/j.tetlet.2014.08.127

    Article  CAS  Google Scholar 

  32. Azath, I.A., Puthiaraj, P., and Pitchumani, K., ACS Sustainable Chem. Eng., 2013, vol. 1, p. 174. https://doi.org/10.1021/sc3000866

    Article  CAS  Google Scholar 

  33. Darbre, T. and Machuqueiro, M., Chem. Commun., 2003, p. 1090. https://doi.org/10.1039/B301117H

  34. Kofoed, J., Machuqueiro, M., Reymond, J.L., and Darbre, T., Chem. Commun., 2004, p. 1540. https://doi.org/10.1039/B404465G

  35. Fernandez-Lopez, R., Kofoed, J., Machuqueiro, M., and Darbre, T., Eur. J. Org. Chem., 2005, p. 5268. https://doi.org/10.1002/ejoc.200500352

  36. Poddar, R., Jain, A., and Kidwai, M., J. Adv. Res., 2017, vol. 8, p. 245. https://doi.org/10.1016/j.jare.2016.12.005

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  37. Yan, S.Q., Guo, W., Wang, W.S., and Zhang, W., Chin. J. Org. Chem., 2019, vol. 39, p. 1469. https://doi.org/10.6023/cjoc201812046

    Article  CAS  Google Scholar 

  38. Kidwai, M. and Jain, A., Appl. Organomet. Chem., 2012, vol. 6, p. 528. https://doi.org/10.1002/aoc.2895

    Article  CAS  Google Scholar 

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  1. School of Petroleum and Chemical Engineering, Dongying Vocational Institute, 257091, Dongying, China

    Zong Han

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Han, Z. Multicomponent Synthesis of Dihydropyrano[2,3-c]pyrazoles Catalyzed by Zinc-Proline Complex. Russ J Org Chem 58, 1297–1302 (2022). https://doi.org/10.1134/S1070428022090159

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