Skip to main content

Advertisement

Log in

Synthesis of indole and its derivatives in water

  • REVIEW
  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Various methodologies for the synthesis of indole and its derivatives in water are described. Different elements ranging from p-block elements, transition metals to lanthanides, along with peptides, surfactants, ionic liquids, and nanoparticles have been used to synthesize either the indole nucleus or its derivatives. The reactions are conducted both in water only and in a mixture of water with an organic solvent, thus holding a great potential to produce libraries of such compounds in water.

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

Access this article

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

Instant access to the full article PDF.

Figure 1

Similar content being viewed by others

References

  1. Alfonsi, K.; Colberg, J.; Dunn, P. J.; Fevig, T.; Jennings, S.; Johnson, T. A.; Kleine, H. P.; Knight, C.; Nagy, M. A.; Perry, D. A.; Stefaniak, M. Green Chem. 2008, 10, 31.

    Article  CAS  Google Scholar 

  2. Jiménez-González, C.; Constable, D. J. C. Green Chemistry and Engineering: A Practical Design Approach; John Wiley & Sons: Hoboken, 2011.

    Google Scholar 

  3. Kabri, Y.; Gellis, A.; Vanelle, P. Green Chem. 2009, 11, 201.

    Article  CAS  Google Scholar 

  4. Constable, D. J. C.; Dunn, P. J.; Hayler, J. D.; Humphrey, G. R.; Leazer, J. L., Jr.; Linderman, R. J.; Lorenz, K.; Manley, J.; Pearlman, B. A.; Wells, A.; Zaks, A.; Zhang, T. Y. Green Chem., 2007, 9, 411.

    Article  CAS  Google Scholar 

  5. Constable, D. J. C.; Curzons, A. D.; Cunningham, V. L. Green Chem. 2002, 4, 521.

    Article  CAS  Google Scholar 

  6. Chemical Synthesis in Supercritical Fluids; Jessop, P. G.; Leitner, W., Eds.; Wiley-VCH: Weinheim, 2008.

  7. Rogers, R. D.; Seddon, K. R. Science 2003, 302, 792.

    Article  Google Scholar 

  8. Chen, D.-H.; Wu, S.-H. Chem. Mater. 2000, 12, 1354.

    Article  CAS  Google Scholar 

  9. Johnston, K. P.; Harrison, K. L.; Clarke, M. J.; Howdle, S. M.; Heitz, M. P.; Bright, F. V.; Carlier, C.; Randolph, T. W. Science 1996, 271, 624.

    Article  CAS  Google Scholar 

  10. Dixneuf, P. H.; Cadierno, V. Metal-Catalyzed Reactions in Water; Wiley-VCH: Weinheim, 2013.

    Book  Google Scholar 

  11. Li, B.; Dixneuf, P. H. Chem. Soc Rev. 2013, 42, 5744.

    Article  CAS  Google Scholar 

  12. Grieco, P. A.; Yoshida, K.; Garner, P. J. Org. Chem. 1983, 48, 3137.

    Article  CAS  Google Scholar 

  13. Kuhl, P.; Könnecke, A.; Döring, G.; Däumer, H.; Jakubke, N.-D. Tetrahedron Lett. 1980, 21, 893.

    Article  CAS  Google Scholar 

  14. Chanda, A.; Fokin, V. V. Chem. Rev. 2009, 109, 725.

    Article  CAS  Google Scholar 

  15. Butler, R. N.; Coyne, A. G. Chem. Rev. 2010, 110, 6302.

    Article  CAS  Google Scholar 

  16. Lindström, U. M. Chem. Rev. 2002, 102, 2751.

    Article  Google Scholar 

  17. Dallinger, D.; Kappe, C. O. Chem. Rev. 2007, 107, 2563.

    Article  CAS  Google Scholar 

  18. Simon, M. O.; Li, C. J. Chem. Soc. Rev. 2012, 41, 1415.

    Article  CAS  Google Scholar 

  19. Li, C. J.; Chen, L. Chem. Soc. Rev. 2006, 35, 68.

    Article  Google Scholar 

  20. Li, C. J.; Chan, T. H. Organic Reactions in Aqueous Media; Wiley-Interscience: New York, 1997.

    Google Scholar 

  21. Li, C.-J. Chem. Rev. 2005, 105, 3095.

    Article  CAS  Google Scholar 

  22. Bhadra, S.; Saha, A.; Ranu, B. C. Green Chem. 2008, 10, 1224.

    Article  CAS  Google Scholar 

  23. Kochanowska-Karamyan, A. J.; Hamann, M. T. Chem. Rev. 2010, 110, 4489.

    Article  CAS  Google Scholar 

  24. Soret, J.; Bakkour, N.; Maire, S.; Durand, S.; Zekri, L.; Gabut, M.; Fic, W.; Divita, G.; Rivalle, C.; Dauzonne, D.; Nguyen, C. H.; Jeanteur, P.; Tazi, J. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 8764.

    Article  CAS  Google Scholar 

  25. Somei, M.; Yamada, F. Nat. Prod. Rep. 2005, 22, 73.

    Article  CAS  Google Scholar 

  26. Hofsteenge, J.; Mueller, D. R.; de Beer, T.; Loeffler, A.; Richter, W. J.; Vliegenthart, J. F. G. Biochemistry 1994, 33, 13524.

    Article  CAS  Google Scholar 

  27. Biswal, S.; Sahoo, U.; Sethy, S.; Kumar, H. K. S.; Banerjee, M. Asian J. Pharm. Clin. Res., 2012, 5, 1.

    CAS  Google Scholar 

  28. Gluckman, M. I.; Baum, T. Psychopharm., 1969, 169.

  29. Aggarwal, B. B.; Ichikawa, H. Cell Cycle 2005, 4, 1201.

    Article  CAS  Google Scholar 

  30. Takayama, H.; Maeda, M.; Ohbayashi, S.: Kitajima, M.; Sakai, S. I.; Aimi, N. Tetrahedron Lett. 1995, 36, 9337.

    Article  CAS  Google Scholar 

  31. Wiley, J. L.; Compton, D. R.; Dai, D.; Lainton, J. A. H.; Phillips, M.; Huffman, J. W.; Martin, B. R. J. Pharmacol. Exp. Ther. 1998, 285, 995.

    CAS  Google Scholar 

  32. Daugan, A.; Grondin, P.; Ruault, C.; Le Monnier de Gouville, A.-C.; Coste, H.; Linget, J. M.; Kirilovsky, J.; Hyafil, F.; Labaudinière, R. J. Med. Chem. 2003, 46, 4533.

    Article  CAS  Google Scholar 

  33. Takayama, H.; Ishikawa, H.; Kurihara, M.; Kitajima, M.; Aimi, N.; Ponglux, D.; Koyama, F.; Matsumoto, K.; Moriyama, T.; Yamamoto, L. T.; Watanabe, K.; Murayama, T.; Horie, S. J. Med. Chem. 2002, 45, 1949.

    Article  CAS  Google Scholar 

  34. Wu, S.; Wang, L.; Guo, W.; Liu, X.; Liu, J.; Wei, X.; Fang, B. J. Med. Chem. 2011, 54, 2668.

    Article  CAS  Google Scholar 

  35. Humphrey, G. R.; Kuethe, J. T. Chem. Rev. 2006, 106, 2875.

    Article  CAS  Google Scholar 

  36. de Sá Alves, F. R.; Barreiro, E. J.; Fraga, C. A. M. Mini-Rev. Med. Chem. 2009, 9, 782.

    Article  Google Scholar 

  37. Trost, B. M.; Brennan, M. K. Synthesis 2009, 3003.

  38. Taber, D. F.; Tirunahari, P. K. Tetrahedron 2011, 67, 7195.

    Article  CAS  Google Scholar 

  39. Sharma, V.; Kumar, P.; Pathak, D. J. Heterocycl. Chem. 2010, 47, 491.

    CAS  Google Scholar 

  40. Gupta, N.; Thakur, A.; Bhardwaj, P. New J. Chem. 2014, 38, 3749.

    Article  CAS  Google Scholar 

  41. Bhirud, S. B.; Sarin, G. S.; Gupta, N.; Tiwari, P. K.; Chidambaram, V. S.; Wadhwa, L. WO Patent 2010140168.

  42. Gupta, N.; Shallu; Kad, G. L.; Singh, J. Nat. Prod. Res. 2014, 28, 424.

    Article  CAS  Google Scholar 

  43. Xu, D.-Q.; Wu, J.; Luo, S.-P.; Zhang, J.-X.; Wu, J.-Y.; Du, X.-H.; Xu, Z.-Y. Green Chem. 2009, 11, 1239.

    Article  CAS  Google Scholar 

  44. Li, B. L.; Xu, D.-Q.; Zhong, A. G. J. Fluorine Chem. 2012, 144, 45.

    Article  CAS  Google Scholar 

  45. Cho, C. S.; Kim, J. H.; Shim, S. C. Tetrahedron Lett. 2000, 41, 1811.

    Article  CAS  Google Scholar 

  46. Hiroya, K.; Itoh, S.; Sakamoto, T. Tetrahedron 2005, 61, 10958.

    Article  CAS  Google Scholar 

  47. Ye, D.; Wang, J.; Zhang, X.; Zhou, Y.; Ding, X.; Feng, E.; Sun, H.; Liu, G.; Jiang, H.; Liu, H. Green Chem. 2009, 11, 1201.

    Article  CAS  Google Scholar 

  48. Layek, M.; Lakshmi, U.; Kalita, D.; Barange, D. K.; Islam, A.; Mukkanti, K.; Pal, M. Beilstein J. Org. Chem. 2009, 5, 46.

    Article  Google Scholar 

  49. Khan, T. A.; Tripoli, R.; Crawford, J. J.; Martin, C. G.; Murphy, J. A. Org. Lett. 2003, 5, 2971.

    Article  CAS  Google Scholar 

  50. Manabe, K.; Aoyama, N.; Kobayashi, S. Adv. Synth. Catal. 2001, 343, 174.

    Article  CAS  Google Scholar 

  51. Xu, R.; Ding, J. C.; Chen, X. A.; Liu, M. C.; Wu, H. Y.; Chinese Chem. Lett. 2009, 20, 676.

    Article  CAS  Google Scholar 

  52. Azizi, N.; Arynasab, F.; Saidi, M. R. Org. Biomol. Chem. 2006, 4, 4275.

    Article  CAS  Google Scholar 

  53. Gu, Y.; Ogawa, C.; Kobayashi, S. Org. Lett. 2007, 9, 175.

    Article  CAS  Google Scholar 

  54. Akagawa, K.; Yamashita, T.; Sakamoto, S.; Kudo, K. Tetrahedron Lett. 2009, 50, 5602.

    Article  CAS  Google Scholar 

  55. Agnusdei, M.; Bandini, M.; Melloni, A.; Umani-Ronchi, A. J. Org. Chem. 2003, 68, 7126.

    Article  CAS  Google Scholar 

  56. Damodiran, M.; Kumar, R. S.; Sivakumar, P. M.; Doble, M.; Perumal, P. T. J. Chem. Sci. 2009, 121, 65.

    Article  CAS  Google Scholar 

  57. Firouzabadi, H.; Iranpoor, N.; Nowrouzi, F. Chem. Commun. 2005, 6, 789.

    Article  Google Scholar 

  58. Wu, P. H.; Wan, Y.; Cai, J. Synlett 2008, 1193.

  59. Habib, P. M.; Kavala, V.; Kuo, C.-W.; Yao, C.-F. Tetrahedron Lett. 2008, 49, 7005.

    Article  CAS  Google Scholar 

  60. Sarkar, S.; Pal, R.; Sen, A. K. Tetrahedron Lett. 2013, 54, 4273.

    Article  CAS  Google Scholar 

  61. Sobhani, S.; Safaei, E.; Hasaninejad, A.-R.; Rezazadeh, S. J. Organomet. Chem. 2009, 694, 3027.

    Article  CAS  Google Scholar 

  62. Zolfigol, M. A.; Salehi, P.; Shiri, M.; Tanbakouchian, Z.; Catal. Commun. 2007, 8, 173.

    Article  CAS  Google Scholar 

  63. Chen, D.; Yu, L.; Wang, P. G. Tetrahedron Lett. 1996, 37, 4467.

    Article  CAS  Google Scholar 

  64. Shirakawa, S.; Kobayashi, S. Org. Lett. 2006, 8, 4939.

    Article  CAS  Google Scholar 

  65. Azizi, N.; Torkian, L.; Saidi, M. R. J. Mol. Cat. A: Chem. 2007, 275, 109.

    Article  CAS  Google Scholar 

  66. Kokare, N. D.; Sangshetti, J. N.; Shinde, D. B. Chin. Chem. Lett. 2008, 19, 1186.

    Article  CAS  Google Scholar 

  67. Hazarika, P.; Sharma, S. D.; Konwar, D. Synth. Commun. 2008, 38, 2870.

    Article  CAS  Google Scholar 

  68. Wang, S.-Y.; Ji, S.-J.; Su, X.-M. Chin. J. Chem. 2008, 26, 22.

    Article  CAS  Google Scholar 

  69. Joshi, R. S.; Mandhane, P. G.; Diwakar, S. D.; Gill, C. H. Ultrason. Sonochem. 2010, 17, 298.

    Article  CAS  Google Scholar 

  70. Pal, R. Int. J. Org. Chem. 2013, 3, 136.

    Article  CAS  Google Scholar 

  71. Meshram, H. M.; Thakur, P. B.; Bejjam, M. B. Green Chem. Lett. Rev. 2013, 6, 95.

    Article  CAS  Google Scholar 

  72. Shanthi, G.; Lakshmi, N. V.; Perumal, P. T. ARKIVOC 2009, x, 121.

  73. Azizian, J.; Mohammadi, A. A.; Karimi, A. R.; Mohammadizadeh, M. R. J. Chem. Res. 2004, 424.

  74. Kumar, V. P.; Reddy, V. P.; Sridhar, R.; Srinivas, B.; Narender, M.; Rao, K. R. J. Org. Chem. 2008, 73, 1646.

    Article  CAS  Google Scholar 

  75. Kumar, S.; Kumar, V.; Chimni, S. S. Tetrahedron Lett. 2003, 44, 2101.

    Article  CAS  Google Scholar 

  76. Prajapati, D.; Gohain, M.; Gogoi, B. J. Tetrahedron Lett. 2006, 47, 3535.

    Article  CAS  Google Scholar 

  77. Zhang, H.-B.; Liu, L.; Chen, Y.-J.; Wang, D.; Li, C.-J. Eur. J. Org. Chem. 2006, 869.

  78. Westermaier, M.; Mayr, H. Org. Lett. 2006, 8, 4791.

    Article  CAS  Google Scholar 

  79. Kokubo, M.; Naito, T.; Kobayashi, S. Tetrahedron 2010, 66, 1111.

    Article  CAS  Google Scholar 

  80. Boudou, M.; Ogawa, C.; Kobayashi, S. Adv. Synth. Catal. 2006, 348, 2585.

    Article  CAS  Google Scholar 

  81. Hikawa, H.; Suzuki, H.; Yokoyama, Y.; Azumaya I., Catalysts 2013, 3, 486.

    Article  CAS  Google Scholar 

  82. Srinivas, V.; Koketsu, M. Tetrahedron 2013, 69, 8025.

    Article  CAS  Google Scholar 

  83. Dandia, A.; Parewa, V.; Jain, A. K.; Rathore, K. S. Green Chem. 2011, 13, 2135.

    Article  CAS  Google Scholar 

  84. Narayanan, R.; El-Sayed, M. A. J. Phys. Chem. B. 2005, 109, 12663.

    Article  CAS  Google Scholar 

  85. Karmakar, B.; Nayak, A.; Banerji, J. Tetrahedron Lett. 2012, 53, 5004.

    Article  CAS  Google Scholar 

  86. Yong, F.-F.; Teo, Y.-C.; Tay, S.-H.; Tan, B. Y.-H.; Lim, K.-H. Tetrahedron Lett. 2011, 52, 1161.

    Article  CAS  Google Scholar 

  87. Abele, E.; Abele, R. Chem. Heterocycl. Compd. 2013, 49, 1384. [Khim. Geterotsikl. Soedin. 2013, 1486.]

    Article  CAS  Google Scholar 

  88. Sharma, A.; Kumar, R.; Sharma, N.; Kumar, V.; Sinha, A. K. Adv. Synth. Catal. 2008, 350, 2910.

    Article  CAS  Google Scholar 

  89. Majumdar, K. C.; Taher, A.; Ponra, S. Tetrahedron Lett. 2010, 51, 147.

    Article  CAS  Google Scholar 

  90. Kotha, S.; Goyal, D.; Chavan, A. S. J. Org. Chem. 2013, 78, 12288.

    Article  CAS  Google Scholar 

  91. Kotha, S. Acc. Chem. Res. 2003, 36, 342.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Neeraj Gupta or Deepti Goyal.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(1), 4–16

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Gupta, N., Goyal, D. Synthesis of indole and its derivatives in water. Chem Heterocycl Comp 51, 4–16 (2015). https://doi.org/10.1007/s10593-015-1651-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-015-1651-3

Keywords

Navigation