Skip to main content
SpringerLink
Log in

Ultrasound-assisted rapid and efficient one-pot synthesis of furanyl spirooxindolo and spiroquinoxalinopyrrolizidines by 1,3-dipolar cycloaddition: a green protocol

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

Efficient synthesis of novel spirooxindolo and spiroquinoxalinopyrrolizidine derivatives was expediently accomplished with regioselectivity via one-pot, three-component 1,3-dipolar cycloaddition using ultrasonication. Chalcones derived from both heteroaryl methyl ketones and furfural were used as dipolarophiles in these reactions. The synthesized compounds were analyzed by 1H and 13C nuclear magnetic resonance (NMR), mass spectrometry, and elemental (CHN) analysis. Single-crystal X-ray diffraction studies of one of the compounds (11d) proved the structure and regiochemistry of the cycloaddition. The ultrasound methodology is clearly advantageous, and the desired products were obtained in moderate to good yield in shorter reaction time compared with conventional heating and fusion methods.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Scheme 2
Scheme 3
Scheme 4
Scheme 5
Scheme 6
Scheme 7
Fig. 1
Fig. 2

Similar content being viewed by others

References

  1. S.J. Tabatabaei Rezaei, M.R. Nabid, A. Yari, S.W.Ng, Ultrason. Sonochem. 18, 49 (2011)

  2. B.H. Rotstein, S. Zaretsky, V. Rai, A.K. Yudin, Chem. Rev. 114, 8323 (2014)

    Article  CAS  Google Scholar 

  3. F. Damkaci, A.J. Szymaniak, Chem. Educ. 91, 943 (2014)

    Article  CAS  Google Scholar 

  4. C.M.R. Volla, I. Atodiresei, M. Rueping, Chem. Rev. 114, 2390 (2014)

    Article  CAS  Google Scholar 

  5. J. Safari, Z. Zarnegar, Ultrason. Sonochem. 21, 1132 (2014)

    Article  CAS  Google Scholar 

  6. E. Pelit, Z. Turgut, Ultrason. Sonochem. 21, 1600 (2014)

    Article  CAS  Google Scholar 

  7. G. Bentabed-Ababsa, A. Derdour, T. Roisnel, J.A. Sáez, P. Pérez, E. Chamorro, L.R. Domingo, F.J. Mongin, Org. Chem. 74, 2120 (2009)

  8. W. Benchouk, S.M. Mekelleche, M.J. Aurell, L.R. Domingo, Tetrahedron, 65, 4644 (2009)

  9. A.K. Nacereddine, W. Yahia, S. Bouacha, A. Djerourou, Tetrahedron Lett. 51, 2617 (2010)

  10. K. Alimohammadi, Y. Sarrafi, M. Tajbakhsh, S. Yeganegi, M. Hamzehloueian, Tetrahedron 67, 1589 (2011)

    Article  CAS  Google Scholar 

  11. A. Bazgir, S. Ahadi, R. Ghahremanzadeh, H.R. Khavasi, P. Mirzaei, Ultrason. Sonochem. 17, 447 (2010)

    Article  CAS  Google Scholar 

  12. M. Dabiri, Z.N. Tisseh, M. Bahramnejad, A. Bazgir, Ultrason. Sonochem. 18, 1153 (2011)

    Article  CAS  Google Scholar 

  13. J. Feng, K. Ablajan, A. Sali, Tetrahedron 70, 484 (2014)

    Article  CAS  Google Scholar 

  14. A. Hasaninejad, S. Firoozi, F. Mandegani, Tetrahedron Lett. 54, 2791 (2013)

    Article  CAS  Google Scholar 

  15. T. Tsubogo, S. Saito, K. Seki, Y. Yamashita, S. Kobayashi, J. Am. Chem. Soc. 130, 13321 (2008)

  16. W. Li, M. Shi, J. Org. Chem. 73, 4151 (2008)

  17. X.X. Yan, Q. Peng, Y. Zhang, K. Zhang, W. Hong, X.L. Hou, Y.D. Wu, Angew. Chem., Int. Ed. 45, 1979 (2006)

  18. M. Ghandi, A. Yari, S.J.T. Rezaei, A. Taheri, Tetrahedron Lett. 50, 4724 (2009)

  19. Y. Yamashita, X. Guo, R. Takashita, J. Am. Chem. Soc. 132, 3262 (2010)

  20. S.Q. Ge, Y.Y. Hua, M. Xia, Ultrason. Sonochem. 16, 232 (2009)

  21. S. Haddad, S. Boudriga, F. Porzio, A. Soldera, M. Askri, M. Knorr, Y. Rousselin, M.M. Kubicki, C. Golz, C. Strohmann, J. Org. Chem. 80, 9064 (2015)

  22. E. Carlos, P. Galvis, V.V. Kouznetsov, Org. Biomol. Chem. 7372 (2013)

  23. K. Revathy, A. Lalitha, RSC Adv. 279 (2014)

  24. F. Yang, J. Sun, H. Gao, C.G.Yan, RSC Adv. 5, 32786 (2015)

  25. J. Častulík, J. Marek, C. Mazal, Tetrahedron 57, 8339 (2001)

    Article  Google Scholar 

  26. P. Shanmugam, B. Viswambharan, S. Madhavan, Org. Lett. 9, 4095 (2007)

    Article  CAS  Google Scholar 

  27. P. Shanmugam, B. Viswambharan, K. Selvakumar, S. Madhavan, Tetrahedron Lett. 49, 2611 (2008)

    Article  CAS  Google Scholar 

  28. G. Periyasami, R. Raghunathan, G. Surendiran, N. Mathivanan, Bioorg. Med. Chem. Lett. 18, 2342 (2008)

    Article  CAS  Google Scholar 

  29. R.R. Kumar, S. Perumal, P. Senthilkumar, P. Yogeeswari, D. Sriram, Tetrahedron 64, 2962 (2008)

    Article  CAS  Google Scholar 

  30. R. Ranjith-Kumar, S. Perumal, Tetrahedron 63, 12220 (2007)

    Article  Google Scholar 

  31. A.R.S. Babu, R. Raghunathan, Tetrahedron Lett. 49, 4618 (2008)

  32. J. Li, J. Wang, Z. Xu, S. Zhu. ACS Comb. Sci. 16, 506 (2014)

  33. A. Thangamani, Eur. J. Med. Chem. 45, 6120 (2010)

    Article  CAS  Google Scholar 

  34. R.J. Bridges, F.E. Lovering, J.M. Humphrey, M.S. Stanley, T.N. Blakely, Bioorg. Med. Chem. Lett. 3, 115 (1993)

    Article  CAS  Google Scholar 

  35. A.R.S. Babu, R. Raghunathan, Tetrahedron Lett. 48, 6809 (2007)

    Article  CAS  Google Scholar 

  36. K. Jadidi, R. Gharemanzadeh, M. Mehrdad, H.R. Darabi, H.R. Khavasi, D. Asgari, Ultrason. Sonochem. 15, 124 (2008)

    Article  CAS  Google Scholar 

  37. A.S. Konev, M.S. Novikov, A.F. Khlebnikov, Tetrahedron Lett. 46, 8337 (2005)

    Article  CAS  Google Scholar 

  38. E. Ramesh, R. Raghunathan, Tetrahedron Lett. 49, 1125 (2008)

    Article  CAS  Google Scholar 

  39. A.S. Amarasekara, T.B. Singh, E. Larkin, M.A. Hasan, H. Fan, Ind. Crop. Prod. 65, 546 (2015)

    Article  CAS  Google Scholar 

  40. Y. Hua, Y. Zou, H. Wu, D. Shi, Ultrason. Sonochem. 19, 264 (2012)

    Article  Google Scholar 

  41. SMART & SAINT. Software Reference manuals. Versions 6.28a & 5.625, Bruker Analytical X-ray Systems Inc., Madison, Wisconsin, USA (2001)

  42. G.M. Sheldrick, SHELXS97 and SHELXL version 2014/7, http://shelx.uniac.gwdg.de/SHELX/index.php

  43. P. Muller, R. Herbst-Imer, A.L. Spek, T.R. Schneider, M. R. Sawaya, in Crystal Structure Refinement: A Crystallographer’s Guide to SHELXL, ed. by P. Muller (Oxford University Press: Oxford, New York, 2006) pp. 57 + XXXV

  44. C.F. Macrae, I.J. Bruno, J.A. Chisholm, P.R. Edgington, P. McCabe, E. Pidcock, L. R-Monge, R. Taylor, J. Van de Streek, P.A. Wood, J. Appl. Cryst. 41, 466 (2008)

  45. L.J. Farrugia, J. Appl. Cryst. 30, 565 (2008)

  46. L.J. Barbour, J. Supramol. Chem. 1, 189 (2001)

Download references

Acknowledgments

S. B. thanks the MHRD, India for the Research Seed Grant. V. B. N. thanks the MHRD, India for the fellowship. S. B. and V. B. N. also thank the Prof. T. Srinivasa Rao, Director, NITW for providing the facilities.

Author information

Authors and Affiliations

  1. Department of Chemistry, National Institute of Technology Warangal, Warangal, Telangana, 506 004, India

    Venkata Bharat Nishtala & Srinivas Basavoju

  2. Centre for X-ray Crystallography, CSIR-Indian Institute of Chemical Technology, Hyderabad, 500 607, India

    Jagadeesh Babu Nanubolu

Authors
  1. Venkata Bharat Nishtala
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jagadeesh Babu Nanubolu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Srinivas Basavoju
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Srinivas Basavoju.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Nishtala, V.B., Nanubolu, J.B. & Basavoju, S. Ultrasound-assisted rapid and efficient one-pot synthesis of furanyl spirooxindolo and spiroquinoxalinopyrrolizidines by 1,3-dipolar cycloaddition: a green protocol. Res Chem Intermed 43, 1365–1381 (2017). https://doi.org/10.1007/s11164-016-2703-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-016-2703-8

Keywords

Search

Navigation