Issue

Vol. 30 No. 7 (2018): Vol 30 Issue 7

Copyright (c) 2018 AJC

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

One-Pot, Green Approach Synthesis of 2-Aryl Substituted Benzimidazole Derivatives Catalyzed by Water Extract of Papaya Bark Ash

https://doi.org/10.14233/ajchem.2018.21296
K. Kantharaju
Department of Chemistry, Peptide and Medicinal Chemistry Research Laboratory, Rani Channamma University, Belagavi-591 156, India
Prashant B. Hiremath
Department of Chemistry, Peptide and Medicinal Chemistry Research Laboratory, Rani Channamma University, Belagavi-591 156, India

Corresponding Author(s) : K. Kantharaju

kk@rcub.ac.in

Asian Journal of Chemistry, Vol. 30 No. 7 (2018): Vol 30 Issue 7

Abstract

A simple, green, rapid and environmentally benign route has been developed for the synthesis of 2-substituted benzimidazoles by the reaction of substituted o-phenylenediamine with different substituted benzoyl chloride using water extract of papaya bark ash (WEPBA) as a green catalyst at room temperature. This method provides several added advantages of being completely green, economic, giving high yields and minimizing use of hazardous solvents. Further, the separated product does not required any kind of chromatographic purification.

Keywords

Green synthesis Benzimidazole o-Phenylenediamine Benzoyl chloride Water extract of papaya bark ash
Kantharaju, K., & Hiremath, P. B. (2018). One-Pot, Green Approach Synthesis of 2-Aryl Substituted Benzimidazole Derivatives Catalyzed by Water Extract of Papaya Bark Ash. Asian Journal of Chemistry, 30(7), 1634–1638. https://doi.org/10.14233/ajchem.2018.21296
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. P.J. Walsh, H. Li and C.A. de Parrodi, Chem. Rev., 107, 2503 (2007); https://doi.org/10.1021/cr0509556.
  2. M. Sarmah, M. Mondal and U. Bora, Chem. Select, 2, 5180 (2017); https://doi.org/10.1002/slct.201700580.
  3. M. Sarmah, A. Dewan, M. Mondal, A.J. Thakur and U. Bora, RSC Adv., 6, 28981 (2016); https://doi.org/10.1039/C6RA00454G.
  4. M. Konwar, A.A. Ali and D. Sarma, Tetrahedron Lett., 57, 2283 (2016); https://doi.org/10.1016/j.tetlet.2016.04.041.
  5. B. Saikia and P. Borah, RSC Adv., 5, 105583 (2015); https://doi.org/10.1039/C5RA20133K.
  6. L.H. Du and P.A. Luo, Synth. Commun., 40, 2880 (2010); https://doi.org/10.1080/00397910903340629.
  7. S. Dinesh, G. Shikha, G. Bhavana, S. Nidhi and S. Dileep, J. Pharm. Scient. Innov., 2, 29 (2012).
  8. Y. Radha, A. Manjula, B.M. Reddy and B.V. Rao, Indian J. Chem., 50B, 1762 (2011).
  9. M. Tatsuta, M. Kataoka, K. Yasoshima, S. Sakakibara, Y. Shogase, M. Shimazaki, T. Yura, Y. Li, N. Yamamoto, J. Gupta and K. Urbahns, Bioorg. Med. Chem. Lett., 2, 2265 (2005); https://doi.org/10.1016/j.bmcl.2005.03.030.
  10. M. Sabat, J.C. VanRens, M.J. Laufersweiler, T.A. Brugel, J. Maier, A. Golebiowski, B. De, V. Easwaran, L.C. Hsieh, R.L. Walter, M.J. Mekel, A. Evdokimov and M.J. Janusz, Bioorg. Med. Chem. Lett., 16, 5973 (2006); https://doi.org/10.1016/j.bmcl.2006.08.132.
  11. L. Sun, D. Chiu, D. Kowal, R. Simon, M. Smeyne, R.S. Zukin, J. Olney, R. Baudy and S. Lin, J. Pharmacol. Exp. Ther., 310, 563 (2004); https://doi.org/10.1124/jpet.104.066092.
  12. I. Borza, É. Bozó, G. Barta-Szalai, C. Kiss, G. Tárkányi, Á. Demeter, T. Gáti, V. Háda, S. Kolok, A. Gere, L. Fodor, J. Nagy, K. Galgóczy, I. Magdó, B. Ágai, J. Fetter, F. Bertha, G.M. Keserü, C. Horváth, S. Farkas, I. Greiner and G. Domány, J. Med. Chem., 50, 901 (2007); https://doi.org/10.1021/jm060420k.
  13. S.A. Smith and R.E. Markwell, Benzimidazoles as 5-Lipoxygenase Inhibitors, US Patent 4925853 (1990).
  14. B.G. Stanley, W. Magdalin, A. Seirafi, M.M. Nguyen and S.F. Leibowitz, Peptides, 13, 581 (1992); https://doi.org/10.1016/0196-9781(92)90093-I.
  15. E.A. Nutescu, N.L. Shapiro and A. Chevalier, Cardiol. Clin., 26, 169 (2008); https://doi.org/10.1016/j.ccl.2007.12.005.
  16. T.D. Penning, G.D. Zhu, J. Gong, S. Thomas, V.B. Gandhi, X. Liu,Y. Shi, V. Klinghofer, E.F. Johnson, C.H. Park, E.H. Fry, C.K. Donawho, D.J. Frost, F.G. Buchanan, G.T. Bukofzer, L.E. Rodriguez, V. BontchevaDiaz, J.J. Bouska, D.J. Osterling, A.M. Olson, K.C. Marsh, Y. Luo and V.L. Giranda, J. Med Chem., 53, 3142 (2010); https://doi.org/10.1021/jm901775y.
  17. Y. Kubota, T. Iwamoto and T. Seki, Nucleic Acids Symp. Ser., 42, 53 (1999); https://doi.org/10.1093/nass/42.1.53.
  18. H.M. Elokdah, S.Y. Chai and T.S. Sulkowski, US Patent 5764473 (1998); Chem. Abstr., 129, 58.784g (1998).
  19. G.A. Kilcigil and N. Altanlar, Turk. J. Chem., 30, 223 (2006).
  20. Maruthamuthu, S. Rajam and C.R. Stella, World J. Pharm. Res., 4, 1853 (2015).
  21. S. Rajam, C.R. Stella and B.R. Venkatraman, J. Chem. Pharm. Res., 4, 2988 (2012).
  22. S. Chandhrasekar, S. Rajam, C.R. Stella and Maruthamuthu, J. Chem. Pharm. Res., 4, 4937 (2012).
  23. P.F. Bocion, C.J. Cattanach, P. Eggenberg, J. Gressel, M.-L. Hagmann, S. Malkin and J. Wenger, Pesticide Biochem. Physiol., 28, 75 (1987); https://doi.org/10.1016/0048-3575(87)90115-5.
  24. J.-M. Yang and C.-C. Chen, Proteins, 55, 288 (2004); https://doi.org/10.1002/prot.20035.
  25. A.A. Spasov, I.N. Yozhitsa, L.I. Bugaeva and V.A. Anisimova, Pharm. Chem. J., 33, 232 (1999); https://doi.org/10.1007/BF02510042.
  26. H. Nakano, T. Inoue, N. Kawasaki, H. Miyataka, H. Matsumoto, T. Taguchi, N. Inagaki, H. Nagai and T. Satoh, Bioorg. Med. Chem., 8, 373 (2000); https://doi.org/10.1016/S0968-0896(99)00291-6.
  27. N.H. Hauel, H. Nar, H. Priepke, U. Ries, J. Stassen and W. Wienen, J. Med. Chem., 45, 1757 (2002); https://doi.org/10.1021/jm0109513.
  28. Y. He, B. Wu, J. Yang, D. Robinson, L. Risen, R. Ranken, L. Blyn, S. Sheng and E.E. Swayze, Bioorg. Med. Chem. Lett., 13, 3253 (2003); https://doi.org/10.1016/S0960-894X(03)00661-9.
  29. A.R. Porcari, R.V. Devivar, L.S. Kucera, J.C. Drach and L.B. Townsend, J. Med. Chem., 41, 1252 (1998); https://doi.org/10.1021/jm970559i.
  30. T. Roth, M.L. Morningstar, P.L. Boyer, S.H. Hughes, R.W. Buckheit and C.J. Michejda, J. Med. Chem., 40, 4199 (1997); https://doi.org/10.1021/jm970096g.
  31. M.T. Migawa, J.-L. Girardet, J.A. Walker, G.W. Koszalka, J.C. Drach, S.D. Chamberlain and L.B. Townsend, J. Med. Chem., 41, 1242 (1998); https://doi.org/10.1021/jm970545c.
  32. J. Mann, A. Baron, Y. Opoku-Boahen, E. Johansson, G. Parkinson, L.R. Kelland and S. Neidle, J. Med. Chem., 44, 138 (2001); https://doi.org/10.1021/jm000297b.
  33. A. Figge, H.J. Altenbach, J.D. Brauer and P. Tielmann, Tetrahedron Asymm., 13, 137 (2002); https://doi.org/10.1016/S0957-4166(02)00079-4.
  34. T. Hisano, M. Ichikawa, K. Tsumoto and M. Tasaki, Chem. Pharm. Bull. (Tokyo), 30, 2996 (1982); https://doi.org/10.1248/cpb.30.2996.
  35. B.V.S. Kumar, S.D. Vaidya, R.V. Kumar, S.B. Bhirud and R.B. Mane, Eur. J. Med. Chem., 41, 599 (2006); https://doi.org/10.1016/j.ejmech.2006.01.006.
  36. R. Katla, R. Chowrasia, P.S. Manjari and N.L.C. Domingues, RSC Adv., 5, 41716 (2015); https://doi.org/10.1039/C4RA16222F.
  37. I. Bhatnagar and M.V. George, Tetrahedron, 24, 1293 (1968); https://doi.org/10.1016/0040-4020(68)88080-9.
  38. K. Bahrami, M.M. Khodaei and F. Naali, J. Org. Chem., 73, 6835 (2008); https://doi.org/10.1021/jo8010232.
  39. N. Zheng, K.W. Anderson, X. Huang, H.N. Nguyen and S.L. Buchwald, Angew. Chem., 46, 7509 (2007); https://doi.org/10.1002/anie.200702542.
  40. P. Beaulieu, B. Haché and E. von Moos, Synthesis, 1683 (2003); https://doi.org/10.1055/s-2003-40888.
  41. J.J. Vanden Eynde, F. Delfosse, P. Lor and Y. van Haverbeke, Tetrahedron, 51, 5813 (1995); https://doi.org/10.1016/0040-4020(95)00252-4.
  42. L.-H. Du and Y.-G. Wang, Synthesis, 675 (2007); https://doi.org/10.1055/s-2007-965922.
  43. P. Gogoi and D. Konwar, Tetrahedron Lett., 47, 79 (2006); https://doi.org/10.1016/j.tetlet.2005.10.134.
  44. M.P. Singh, S. Sasmal, W. Lu and M.N. Chatterjee, Synthesis, 1380 (2000); https://doi.org/10.1055/s-2000-7111.
  45. X. Wang, L. Zhang, Y. Xu, D. Krishnamurthy and C.H. Senanayake, Tetrahedron Lett., 45, 7167 (2004); https://doi.org/10.1016/j.tetlet.2004.07.042.
  46. A.B. Alloum, K. Bougrin and M. Soufiaoui, Tetrahedron Lett., 44, 5935 (2003); https://doi.org/10.1016/S0040-4039(03)01387-X.
  47. D. Yang, H. Fu, L. Hu, Y. Jiang and Y. Zhao, J. Org. Chem., 73, 7841 (2008); https://doi.org/10.1021/jo8014984.
  48. S.C. Subramanyam and S. Narayanan, Int. J. Appl. Biol. Pharm. Technol., 1, 689 (2010).
  49. S. Lin and L. Yang, Tetrahedron Lett., 46, 4315 (2005); https://doi.org/10.1016/j.tetlet.2005.04.101.
  50. R.N. Nadaf, S.A. Siddiqui, T. Daniel, R.J. Lahoti and K.V. Srinivasan, J. Mol. Catal. A, 214, 155 (2004); https://doi.org/10.1016/j.molcata.2003.10.064.
  51. M.M. Heravi, S. Sadjadi, H.A. Oskooie, R.H. Shoar and F.F. Bamoharram, Catal. Commun., 9, 504 (2008); https://doi.org/10.1016/j.catcom.2007.03.011.
  52. B. Das, H. Holla and Y. Srinivas, Tetrahedron Lett., 48, 61 (2007); https://doi.org/10.1016/j.tetlet.2006.11.018.
  53. B. Zou, Q. Yuan and D. Ma, Angew. Chem., 46, 2598 (2007); https://doi.org/10.1002/anie.200700071.
  54. R. Varala, A. Nasreen, R. Enugala and R.S. Adapa, Tetrahedron Lett., 48, 69 (2007); https://doi.org/10.1016/j.tetlet.2006.11.010.
  55. C.-H. Wu and C.-M. Sun, Tetrahedron Lett., 47, 2601 (2006); https://doi.org/10.1016/j.tetlet.2006.02.015.
  56. M.P. Surpur, P.R. Singh, S.B. Patil and S.D. Samant, Synth. Commun., 37, 1375 (2007); https://doi.org/10.1080/00397910701230170.
  57. Z. Mao, Z. Wang, J. Li, X. Song and Y. Luo, Synth. Commun., 40, 1963 (2010); https://doi.org/10.1080/00397910903219328.
  58. K. Kantharaju and P.B. Hiremath, Int. J. Eng. Technol. Sci. Res., 4, 807 (2017).
  59. K. Kantharaju and S.Y. Khatavi, Int. J. Eng. Technol. Sci. Res., 4, 510 (2017).
  60. J.Y. Hao, Z.Y. Ge and S.Y. Yang, Synth. Commun., 33, 79 (2003); https://doi.org/10.1081/SCC-120015562.
  61. N.J. Coville and E.W. Neuse, J. Org. Chem., 42, 3485 (1977); https://doi.org/10.1021/jo00442a007.
  62. V.K. Tandon and M. Kumar, Tetrahedron Lett., 45, 4185 (2004); https://doi.org/10.1016/j.tetlet.2004.03.117.
  63. S.B. Khalili and A.R. Sardarian, Monatsh. Chem., 143, 841 (2012); https://doi.org/10.1007/s00706-011-0647-7.
  64. S. Neidle, E.L. Rayner, I.J. Simpson, N.J. Smith, J. Mann, A. Baron, Y. OpokuBoahen, K.R. Fox, J.A. Hartley and L.R. Kelland, Chem. Commun., 929 (1999); https://doi.org/10.1039/a901074b.
  65. K. Bougrin, A. Loupy and M. Soufiaoui, Tetrahedron, 54, 8055 (1998); https://doi.org/10.1016/S0040-4020(98)00431-1.
Read More
Author biographies is not available.
Download
PDF
Statistic
Read Counter : 0 Download : 0