Skip to main content
SpringerLink
Log in

Intramolecular cyclization of N-propargyl anilines: a new synthetic entry into highly substituted indoles

  • Original Paper
  • Published:
Journal of the Iranian Chemical Society Aims and scope Submit manuscript

Abstract

Indole derivatives are an important class of heterocycle found in a large number of natural products and synthetic pharmaceuticals. Given the low cost and easy availability of N-propargyl anilines, synthesis of indole cores from these versatile structural motifs has attracted a lot of attention in the past decade. In this review, we summarize the most representative and interesting reports on this rapidly advancing area, with special emphasis on mechanistic aspects of the reactions.

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

Fig. 1
Fig. 2
Fig. 3
Scheme 1
Scheme 2
Scheme 3
Scheme 4
Scheme 5
Scheme 6
Scheme 7
Scheme 8
Scheme 9
Scheme 10
Scheme 11
Scheme 12
Scheme 13
Scheme 14
Scheme 15
Scheme 16
Scheme 17
Scheme 18
Scheme 19
Scheme 20
Scheme 21
Scheme 22
Scheme 23

Similar content being viewed by others

References

  1. M. Ishikura, T. Abe, T. Choshi, S. Hibino, Nat. Prod. Rep. 30, 694–752 (2013)

    Article  CAS  Google Scholar 

  2. I.S. Marcos, R.F. Moro, I. Costales, P. Basabe, D. Díez, Nat. Prod. Rep. 30, 1509–1526 (2013)

    Article  CAS  Google Scholar 

  3. A. Ndagijimana, X. Wang, G. Pan, F. Zhang, H. Feng, O. Olaleye, Fitoterapia 86, 35–47 (2013)

    Article  CAS  Google Scholar 

  4. J.-H. Lee, J. Lee, FEMS. Microbiol. Rev. 34, 426–444 (2010)

    CAS  Google Scholar 

  5. N.K. Kaushik, N. Kaushik, P. Attri, N. Kumar, C.H. Kim, A.K. Verma, E.H. Choi, Molecules 18, 6620–6662 (2013)

    Article  CAS  Google Scholar 

  6. T. Sravanthi, S. Manju, Eur. J. Pharm. Sci. 91, 1–10 (2016)

    Article  CAS  Google Scholar 

  7. M.-Z. Zhang, Q. Chen, G.-F. Yang, Eur. J. Med. Chem. 89, 421–441 (2015)

    Article  CAS  Google Scholar 

  8. M.T. El-sayed, N.A. Hamdy, D.A. Osman, K.M. Ahmed, Adv. Mod. Oncol. Res. 1, 20–35 (2015)

    Article  Google Scholar 

  9. D. Kerzarea, P. Khedekar, J. Pharm. Sci. Biosci. Res. 6, 144–156 (2016)

    Google Scholar 

  10. S. Biswal, U. Sahoo, S. Sethy, H. Kumar, M. Banerjee, Asian J. Pharm.Clin. Res. 5, 1–6 (2012)

    CAS  Google Scholar 

  11. K. Hemalatha, G. Madhumitha, S.M. Roopan, Chem. Sci. Rev. Lett. 2, 287–292 (2013)

    Google Scholar 

  12. R.B. Mujumdar, L.A. Ernst, S.R. Mujumdar, C.J. Lewis, A.S. Waggoner, Bioconjug. Chem. 4, 105–111 (1993)

    Article  CAS  Google Scholar 

  13. R.M. El-Shishtawy, P. Almeida, Tetrahedron 62, 7793–7798 (2006)

    Article  CAS  Google Scholar 

  14. Z. Seferoğlu, N. Ertan, G. Kickelbick, T. Hökelek, Dyes. Pigm. 82, 20–25 (2009)

    Article  Google Scholar 

  15. Y. Wang, Z. Wan, C. Jia, X. Yao, Synth. Met. 211, 40–48 (2016)

    Article  CAS  Google Scholar 

  16. A. Andreani, M. Rambaldi, J. Heterocyclic Chem. 25, 1519–1523 (1988)

    Article  CAS  Google Scholar 

  17. A. Andreani, A. Locatelli, M. Rambaldi, J. Heterocyclic Chem. 32, 49–51 (1995)

    Article  CAS  Google Scholar 

  18. A. Prabhu, M. Filippi, Int. J. Pest. Manag. 39, 347–353 (1993)

    Article  CAS  Google Scholar 

  19. J. Yang, Q. Wu, R. Liu, S. Ma, C. Liu, Agrochemicals 47, 402–405 (2008)

    CAS  Google Scholar 

  20. B. Robinson, Chem. Rev. 63, 373–401 (1963)

    Article  Google Scholar 

  21. A. Bischler, Ber. Dtsch. Chem. Ges. 25, 2860–2879 (1892)

    Article  Google Scholar 

  22. H. Hemetsberger, D. Knittel, Monatsh. Chem. 103, 194–204 (1972)

    Article  CAS  Google Scholar 

  23. R.D. Clark, D.B. Repke, Heterocycles 22, 195–221 (1984)

    Article  CAS  Google Scholar 

  24. P.G. Gassman, T. Van Bergen, G. Gruetzmacher, J. Am. Chem. Soc. 95, 6508–6509 (1973)

    Article  CAS  Google Scholar 

  25. G. Bartoli, G. Palmieri, M. Bosco, R. Dalpozzo, Tetrahedron Lett. 30, 2129–2132 (1989)

    Article  CAS  Google Scholar 

  26. S. Cacchi, G. Fabrizi, Chem. Rev. 105, 2873–2920 (2005)

    Article  CAS  Google Scholar 

  27. M. Platon, R. Amardeil, L. Djakovitch, J.-C. Hierso, Chem. Soc. Rev. 41, 3929–3968 (2012)

    Article  CAS  Google Scholar 

  28. L. El Kaim, M. Gizzi, L. Grimaud, Org. Lett. 10, 3417–3419 (2008)

    Article  Google Scholar 

  29. O. Leogane, H. Lebel, Angew. Chem. Int. Ed. 47, 350–352 (2008)

    Article  CAS  Google Scholar 

  30. K. Matcha, A.P. Antonchick, Angew. Chem. Int. Ed. 53, 11960–11964 (2014)

    Article  CAS  Google Scholar 

  31. Q. Sha, H. Arman, M.P. Doyle, Org. Lett. 17, 3876–3879 (2015)

    Article  CAS  Google Scholar 

  32. Y. Ohta, H. Chiba, S. Oishi, N. Fujii, H. Ohno, J. Org. Chem. 74, 7052–7058 (2009)

    Article  CAS  Google Scholar 

  33. B. Li, S. Guo, J. Zhang, X. Zhang, X. Fan, J. Org. Chem. 80, 5444–5456 (2015)

    Article  CAS  Google Scholar 

  34. F. Yang, K.-G. Ji, S. Ali, Y.-M. Liang, J. Org. Chem. 76, 8329–8335 (2011)

    Article  CAS  Google Scholar 

  35. E. Vessally, RSC Adv. 6, 18619–18631 (2016)

    Article  CAS  Google Scholar 

  36. E. Vessally, A. Hosseinian, L. Edjlali, A. Bekhradnia, M.D. Esrafili, RSC Adv. 6, 71662–71675 (2016)

    Article  CAS  Google Scholar 

  37. E. Vessally, L. Edjlali, A. Hosseinian, A. Bekhradnia, M.D. Esrafili, RSC Adv. 6, 49730–49746 (2016)

    Article  CAS  Google Scholar 

  38. E. Vessally, A. Hosseinian, L. Edjlali, A. Bekhradnia, M. D. Esrafili, Curr. Org. Synth. 14, 557–567 (2017)

  39. E. Vessally, A. Hosseinian, L. Edjlali, A. Bekhradnia, M.D. Esrafili, RSC Adv. 6, 99781–99793 (2016)

    Article  CAS  Google Scholar 

  40. B. Thyagarajan, J. Hillard, K. Reddy, K. Majumdar, Tetrahedron Lett. 15, 1999–2002 (1974)

    Article  Google Scholar 

  41. K. Majumdar, G. Jana, J. Chem. Soc. Perkin Trans. 1, 1229–1232 (1997)

  42. P. Magnus, I.S. Mitchell, Tetrahedron Lett. 39, 4595–4598 (1998)

    Article  CAS  Google Scholar 

  43. A. Saito, A. Kanno, Y. Hanzawa, Angew. Chem. 119, 4005–4007 (2007)

    Article  Google Scholar 

  44. A. Saito, S. Oda, H. Fukaya, Y. Hanzawa, J. Org. Chem. 74, 1517–1524 (2009)

    Article  CAS  Google Scholar 

  45. N. Sakai, K. Enomoto, M. Takayanagi, T. Konakahara, Y. Ogiwara, Tetrahedron Lett. 57, 2175–2178 (2016)

    Article  CAS  Google Scholar 

  46. B. Rajagopal, C.-H. Chou, C.-C. Chung, P.-C. Lin, Org. Lett. 16, 3752–3755 (2014)

    Article  CAS  Google Scholar 

  47. N. Kern, M. Hoffmann, A. Blanc, J. Weibel, P. Pale, Org. Lett. 15, 836–839 (2013)

    Article  CAS  Google Scholar 

  48. M. Taguchi, Y. Tokimizu, S. Oishi, N. Fujii, H. Ohno, Org. Lett. 17, 6250–6253 (2015)

    Article  CAS  Google Scholar 

  49. J. Inanaga, O. Ujikawa, M. Yamaguchi, Tetrahedron Lett. 32, 1737–1740 (1991)

    Article  CAS  Google Scholar 

  50. D. L. Boger, R. S. Coleman, ‎J. Am. Chem. Soc. 110, 4796–4807 (1988)

  51. S. N. Osipov, N. M. Kobel’kova, A. F. Kolomiets, K. Pumpor, B. Koksch, K. Burger, Synlett. 1287–1289 (2001)

  52. F. Bellezza, A. Cipiciani, R. Ruzziconi, S. Spizzichino, J. Fluorine Chem. 129, 97–107 (2008)

    Article  CAS  Google Scholar 

  53. J.P. Dittami, H. Ramanathan, Tetrahedron Lett. 29, 45–48 (1988)

    Article  CAS  Google Scholar 

  54. H. Lin, U. Kazmaier, Eur. J. Org. Chem. 2009, 1221–1227 (2009)

  55. S. Kundal, S. Jalal, K. Paul, U. Jana, Eur. J. Org. Chem. 2015, 5513–5517 (2015)

  56. J.A. Murphy, T.A. Khan, S.Z. Zhou, D.W. Thomson, M. Mahesh, Angew. Chem. Int. Ed. 44, 1356–1360 (2005)

    Article  CAS  Google Scholar 

  57. G.P. da Silva, A. Ali, R.C. da Silva, H. Jiang, M.W. Paixão, ‎Chem. Commun. 51, 15110–15113 (2015)

    Article  Google Scholar 

  58. J.D. Nguyen, E.M. D’Amato, J.M. Narayanam, C.R. Stephenson, Nat. Chem. 4, 854–859 (2012)

    Article  CAS  Google Scholar 

  59. R. Grigg, V. Sridharan, Tetrahedron Lett. 33, 7965–7968 (1992)

    Article  CAS  Google Scholar 

  60. D. Brown, R. Grigg, V. Sridharan, V. Tambyrajah, M. Thornton-Pett, Tetrahedron 54, 2595–2606 (1998)

    Article  CAS  Google Scholar 

  61. M. Ishikura, N. Takahashi, K. Yamada, R. Yanada, Tetrahedron 62, 11580–11591 (2006)

    Article  CAS  Google Scholar 

  62. Z. Liu, Y. Xia, S. Zhou, L. Wang, Y. Zhang, J. Wang, Org. Lett. 15, 5032–5035 (2013)

    Article  CAS  Google Scholar 

  63. C.M. Le, P.J.C. Menzies, D.A. Perone, M. Lautens, Angew. Chem. 127, 256–259 (2015)

    Article  Google Scholar 

  64. F. Le Strat, J. Maddaluno, Org. Lett. 4, 2791–2793 (2002)

    Article  Google Scholar 

  65. R. Lhermet, M. Ahmad, C. Fressigné, B. Silvi, M. Durandetti, J. Maddaluno, Chem. Eur. J. 20, 10249–10254 (2014)

    Article  CAS  Google Scholar 

  66. M. Durandetti, L. Hardou, R. Lhermet, M. Rouen, J. Maddaluno, Chem. Eur. J. 17, 12773–12783 (2011)

    Article  CAS  Google Scholar 

  67. H. Fuwa, M. Sasaki, Org. Biomol. Chem. 5, 2214–2218 (2007)

    Article  CAS  Google Scholar 

  68. M.-G. Braun, M.H. Katcher, A.G. Doyle, ‎Chem. Sci. 4, 1216–1220 (2013)

    Article  CAS  Google Scholar 

  69. S. He, R.P. Hsung, W.R. Presser, Z.-X. Ma, B.J. Haugen, Org. Lett. 16, 2180–2183 (2014)

    Article  CAS  Google Scholar 

  70. H. Iwasaki, K. Suzuki, M. Yamane, S. Yoshida, N. Kojima, M. Ozeki, M. Yamashita, Org. Biomol. Chem. 12, 6812–6815 (2014)

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Payame Noor University, Tehran, Iran

    Esmail Vessally

  2. Department of Engineering Science, College of Engineering, University of Tehran, P.O. Box 11365-4563, Tehran, Iran

    Akram Hosseinian

  3. Department of Chemistry, Tabriz Branch, Islamic Azad University, Tabriz, Iran

    Ladan Edjlali, Ebrahim Ghorbani-Kalhor & Rahim Hosseinzadeh-Khanmiri

Authors
  1. Esmail Vessally
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Akram Hosseinian
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ladan Edjlali
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Ebrahim Ghorbani-Kalhor
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Rahim Hosseinzadeh-Khanmiri
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ladan Edjlali.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Vessally, E., Hosseinian, A., Edjlali, L. et al. Intramolecular cyclization of N-propargyl anilines: a new synthetic entry into highly substituted indoles. J IRAN CHEM SOC 14, 2339–2353 (2017). https://doi.org/10.1007/s13738-017-1170-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-017-1170-5

Keywords

Search

Navigation