Skip to main content
SpringerLink
Log in

Ultrasound-promoted regioselective and stereoselective synthesis of novel spiroindanedionepyrrolizidines by multicomponent 1,3-dipolar cycloaddition of azomethine ylides

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

Abstract

A series of novel spiroindanedionepyrrolizidines have been synthesized by multicomponent 1,3-dipolar cycloaddition of a variety of (E)-3-aryl-1-(thiophen-2-yl)prop-2-en-1-ones with unstabilized azomethine ylides generated from ninhydrin and l-proline. The reactions were highly regioselective and stereoselective and were conducted with both conventional heating and ultrasonic irradiation conditions. In general, milder conditions, and moderate improvement in rates, reaction times, and yields were observed when the reactions were performed under ultrasonic conditions. The regioselective and stereoselective nature of the products was established by use of single-crystal X-ray structure and spectroscopic techniques.

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
Fig. 1
Fig. 2
Scheme 2

Similar content being viewed by others

References

  1. R.V.A. Orru, M. de Greef, Synthesis 1471 (2003)

  2. G. Balme, E. Bossharth, N. Monteiro, Eur. J. Org. Chem. 4101 (2003)

  3. S. Brase, C. Gil, K. Knepper, Bioorg. Med. Chem. 10, 2415 (2002)

    Article  Google Scholar 

  4. A. Domling, I. Ugi, Angew. Chem. Int. Ed. 39, 3168 (2000)

    Article  CAS  Google Scholar 

  5. H. Ohno, Y. Ohta, S. Oishi, N. Fujii, Angew. Chem. Int. Ed 46, 2295 (2007)

    Article  CAS  Google Scholar 

  6. D. Bonne, M. Dekhane, J. Zhu, Angew. Chem. Int. Ed. 46, 2485 (2007)

    Article  CAS  Google Scholar 

  7. A. Pinto, L. Neuville, J. Zhu, Angew. Chem. Int. Ed. 46, 3291 (2007)

    Article  CAS  Google Scholar 

  8. S. Komagawa, S. Saito, Angew. Chem. Int. Ed. 45, 2446 (2006)

    Article  CAS  Google Scholar 

  9. H. Yoshida, H. Fukushima, J. Ohshita, A. Kunai, J. Am. Chem. Soc. 128, 11040 (2006)

    Article  CAS  Google Scholar 

  10. H.A. Dondas, C.W.G. Fishwick, X. Gai, R. Grigg, C. Kilner, N. Dumrongchai, B. Kongkathip, N. Kongkathip, C. Polysuk, V. Sridharan, Angew. Chem. Int. Ed. 44, 7570 (2005)

    Article  CAS  Google Scholar 

  11. S. Pache, M. Lautens, Org. Lett. 5, 4827 (2003)

    Article  CAS  Google Scholar 

  12. A.R. Siamaki, B.A. Arndtsen, J. Am. Chem. Soc. 128, 6050 (2006)

    Article  CAS  Google Scholar 

  13. X.H. Duan, X.Y. Liu, L.N. Guo, M.C. Liao, W.M. Liu, Y.M. Liang, J. Org. Chem. 70, 6980 (2005)

    Article  CAS  Google Scholar 

  14. L.F. Tietze, G. Brasche, in Domino Reactions in Organic Synthesis, ed. by K. Gericke (Wiley-VCH, Weinheim, 2006)

    Chapter  Google Scholar 

  15. J. Zhu, in Multicomponent Reactions, ed. by H. Bienayme (Wiley-VCH, Weinheim, 2005)

    Chapter  Google Scholar 

  16. R. Huisgen, Angew. Chem. Int. Ed. Engl. 2, 565 (1963)

    Article  Google Scholar 

  17. R.B. Woodward, R. Hoffmann, Angew. Chem. Int. Ed. Engl. 8, 781 (1969)

    Article  CAS  Google Scholar 

  18. K.N. Houk, J. Sims, R.E. Duke, R.W. Strozier, J.K. George, J. Am. Chem. Soc. 95, 7287 (1973)

    Article  CAS  Google Scholar 

  19. K.N. Houk, J. Sims, C.R. Watts, L.J. Luskus, J. Am. Chem. Soc. 95, 7301 (1973)

    Article  CAS  Google Scholar 

  20. H. Pellissier, Tetrahedron 63, 3235 (2007)

    Article  CAS  Google Scholar 

  21. T.M.V.D. Pinhoe Melo, Eur. J. Org. Chem. 2873 (2006)

  22. G. Pandey, P. Banerjee, S.R. Gadre, Chem. Rev. 106, 4484 (2006)

    Article  CAS  Google Scholar 

  23. I. Coldham, R. Hufton, Chem. Rev. 105, 2765 (2005)

    Article  CAS  Google Scholar 

  24. K. Ruck-Braun, T.H.E. Freysoldt, F. Wierschem, Chem. Soc. Rev. 34, 507 (2005)

    Article  Google Scholar 

  25. S. Kanemasa, Synlett 1371 (2002)

  26. C. Najera, J.M. Sansano, Curr. Org. Chem. 7, 1105 (2003)

    Article  CAS  Google Scholar 

  27. L.M. Harwood, R.J. Vickers, in Synthetic Application of 1, 3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products, ed. by A. Padwa, W.H. Pearson (Wiley, New York, 2002)

    Google Scholar 

  28. K.V. Gothelf, in Cycloaddition Reactions in Organic Synthesis, ed. by S. Kobaya-Shi, K.A. Jorgensen (Wiley-VCH, Weinheim, 2002)

    Google Scholar 

  29. S. Karlsson, H.E. Hogberg, Org. Prep. Proced. Int. 33, 103 (2001)

    Article  CAS  Google Scholar 

  30. K.V. Gothelf, K.A. Jorgensen, Chem. Rev. 98, 863 (1998)

    Article  CAS  Google Scholar 

  31. R. Sustmann, W. Sicking, R. Huisgen, J. Org. Chem. 58, 82 (1993)

    Article  CAS  Google Scholar 

  32. R. Huisgen, H. Graf, J. Org. Chem. 44, 2595 (1979)

    Article  CAS  Google Scholar 

  33. J.W. Daly, T.F. Spande, N. Whittaker, R.J. Highet, D. Feigl, N. Nishimori, T. Tokuyama, C.W. Meyers, J. Nat. Prod. 49, 265 (1986)

    Article  CAS  Google Scholar 

  34. H. Waldmann, Synlett 133 (1995)

  35. M.A. Abou-Gharbia, P.H. Doukas, Heterocycles 12, 637 (1979)

    Article  CAS  Google Scholar 

  36. M.J. Kornet, A.P. Thio, J. Med. Chem. 19, 892 (1976)

    Article  CAS  Google Scholar 

  37. S.T. Hilton, T.C.T. Ho, G. Pljevaljcic, K. Jones, Org. Lett. 2, 2639 (2000)

    Article  CAS  Google Scholar 

  38. T. Okita, M. Isobe, Tetrahedron 50, 11143 (1994)

    Article  CAS  Google Scholar 

  39. P. Rosenmond, M. Hosseini-Merescht, C. Bub, Liebigs Ann. Chem. 2, 151 (1994)

    Article  Google Scholar 

  40. F. Cataldo, D. Heymann, Fullerene Sci. Technol. 7, 725 (1999)

    Article  CAS  Google Scholar 

  41. K.S. Suslick, in Ultrasound Its Chemical, Physical and Biological Effect, ed. by K.S. Suslick (VCH Publishers, Weinheim, 1989)

    Google Scholar 

  42. J. Castulik, J. Marek, C. Mazal, Tetrahedron 57, 8339 (2001)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  47. R.R. Kumar, S. Perumal, Tetrahedron 63, 12220 (2007)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  51. E. Ramesh, R. Raghanatham, Tetrahedron Lett. 49, 1125 (2008)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  54. R.T. Pardasani, P. Pardasani, V. Chaturvedi, S.K. Yadav, A. Saxena, I. Sharma, Heteroat. Chem. 14, 36 (2003)

    Article  CAS  Google Scholar 

  55. The crystal structure has been deposited at the Cambridge Crystallographic Data centre CCDC number: 772736, molecular formula: C26H20FNO3S, unit cell parameters: a 8.6028(15), b 11.431(2), c 22.242(4), β 95.918(9), space group P21/c. Data acquisition: The Cambridge Crystallographic Data Center;deposit@ccdc.cam.ac.uk, http://www.ccdc.cam.ac.uk/deposit

  56. S. Koda, A. Suzuki, H. Nomura, Polym. J. 27, 1144 (1995)

    Article  CAS  Google Scholar 

  57. Y. Kojima, S. Koda, H. Nomura, Ultrason. Sonochem. 8, 75 (2001)

    Article  CAS  Google Scholar 

  58. R. Huisgen, K.N. Houk, K. Yamaguchi, in 1, 3-Dipolar Cycloaddition Chemistry, ed. by A. Padwa (Wiley, New York, 1984)

    Google Scholar 

  59. R. Huisgen, J. Org. Chem. 41, 403 (1976)

    Article  CAS  Google Scholar 

  60. K.N. Houk, J. Gonzalez, Acc. Chem. Res. 28, 81 (1995)

    Article  CAS  Google Scholar 

  61. J. Lindley, T.J. Mason, Chem. Soc. Rev. 16, 275 (1987)

    Article  CAS  Google Scholar 

  62. J.P. Lorimer, T.J. Mason, Chem. Soc. Rev. 16, 239 (1987)

    Article  CAS  Google Scholar 

  63. J.L. Luche, Synthetic Organic Sonochemistry (Plenum Press, New York, 1998)

    Google Scholar 

  64. C. Einhorn, J.L. Einhorn, Synthesis 11, 787 (1989)

    Article  Google Scholar 

  65. G.M. Sheldrick, SHELXS-97 Program for the solution of Crystal Structures (University of Gottingen, Germany, 1997)

    Google Scholar 

  66. A.L. Spek, PLATON, in: A Multipurpose Crystallographic Tool (Utrecht University, Utrecht, 1999)

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Karpagam University, Coimbatore, 641 021, Tamil Nadu, India

    Elangovann Chandralekha & Arumugam Thangamani

  2. Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati, 781039, India

    Arumugam Thangamani

  3. Chemistry Wing, DDE, Annamalai University, Annamalai Nagar, 608 002, Tamil Nadu, India

    Ramiah Valliappan

Authors
  1. Elangovann Chandralekha
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Arumugam Thangamani
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ramiah Valliappan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Arumugam Thangamani or Ramiah Valliappan.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Chandralekha, E., Thangamani, A. & Valliappan, R. Ultrasound-promoted regioselective and stereoselective synthesis of novel spiroindanedionepyrrolizidines by multicomponent 1,3-dipolar cycloaddition of azomethine ylides. Res Chem Intermed 39, 961–972 (2013). https://doi.org/10.1007/s11164-012-0608-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-012-0608-8

Keywords

Search

Navigation