Skip to main content
SpringerLink
Log in

A mild and expedient one-pot synthesis of substituted benzimidazoles in water using a phase-transfer catalyst

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

1-Alkyl/phenyl-2-arylbenzimidazoles have been synthesized in very good to excellent yields by a one-pot condensation of N-alkyl/phenyl-o-phenylenediamines with aryl aldehydes in water at room temperature using cetylpyridinium bromide as a cheap and eco-friendly catalyst.

Graphical abstract

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

Similar content being viewed by others

References

  1. McKellar QA, Jackson F (2004) Trends Parasitol 20:456

    Article  CAS  Google Scholar 

  2. Velik J, Baliharová V, Fink-Gremmels J, Bull S, Lamka J, Skálová L (2004) Res Vet Sci 76:95

    Article  CAS  Google Scholar 

  3. Köhler P (2001) Int J Parasitol 31:336

    Article  Google Scholar 

  4. American Medical Association (1980) AMA drugs evaluations Wiley, New York, p 1409

  5. Porcari AR, Devivar RV, Kucera LS, Drach JC, Townsend LB (1998) J Med Chem 41:1252

    Article  CAS  Google Scholar 

  6. Migawa MT, Girardet JL, Walker JA, Koszalka GW, Chamberlain SD, Drach JC, Townsend LB (1998) J Med Chem 41:1242

    Article  CAS  Google Scholar 

  7. Roth T, Morningstar ML, Boyer PL, Hughes SH, Buckheit RW Jr, Michejda CJ (1997) J Med Chem 40:4199

    Article  CAS  Google Scholar 

  8. Tamm I, Sehgal PB (1978) Adv Virus Res 22:187

    Article  CAS  Google Scholar 

  9. Tamm I (1957) Science 126:1235

    Google Scholar 

  10. Scott LJ, Dunn CJ, Mallarkey G, Sharpe M (2002) Drugs 62:1503 (Antiulcerative)

  11. Tan R-H, Ding L-C, Wei X-J (2001) Chin J Med Chem 11:259 (Antiinflammatory)

    Google Scholar 

  12. Al Muhaimeed HJ (1997) Int Med Res 25:175 (Antihistaminic)

    Google Scholar 

  13. Skalitzky DJ, Marakovits JT, Maegley KA, Ekker A, Yu X-H, Hostomsky Z, Webber SE, Eastman BW, Almassy R, Li J, Curtin NJ, Newell DR, Calvert AH, Griffin RJ, Golding BT (2003) J Med Chem 46:210

    Article  CAS  Google Scholar 

  14. Easmon J, Puerstinger G, Roth T, Fiebig HH, Jenny M, Jäger W, Heinisch G, Hofmann J (2001) Int J Cancer 94:89

    Article  CAS  Google Scholar 

  15. Mason JS, Morize I, Menard PR, Cheney DL, Hume C, Labaudiniere RF (1999) J Med Chem 42:3251

    Article  CAS  Google Scholar 

  16. Evans BE, Rittle KE, Bock MG, Dipardo RM, Freidinger RM, Whitter WL, Lundell GF, Veber DF, Anderson PS, Chang RS, Chang RSL, Lotti VJ, Gerino DJ, Chen TB, Kling PJ, Kunkel KA, Springer JP, Hirshfield J (1988) J Med Chem 31:2235

    Article  CAS  Google Scholar 

  17. Grimmett MR (2002) Product class 4: benzimidazoles. In: Neier RR (ed) Science of synthesis. George-Thieme, Stuttgart, p 529

    Google Scholar 

  18. Grimmett MR (1984) Imidazoles and their benzo derivatives. In: Katritzky AR, Rees CW (eds) Comprehensive heterocyclic chemistry, vol 5. Oxford, Pergamon, p 457

    Google Scholar 

  19. Preston PN (1981) Benzimidazoles and congeneric tricyclic compounds. In: Weissberger A, Taylor EC (eds) Chemistry of heterocyclic compounds, part 1, vol 40. Wiley, New York, p 6

    Google Scholar 

  20. Preston PN (1974) Chem Rev 74:279

    Article  CAS  Google Scholar 

  21. Tagawa Y, Yamagata K, Sumoto K (2008) Heterocycles 75:415 (Activated C–O2/xylenes)

  22. Bahrami K, Khodaei MM, Kavianinia I (2007) Synthesis:547 (H2O2–HCl)

  23. Du L-H, Wang Y-G (2007) Synthesis:675 (IBD)

  24. Das B, Holla H, Srinivas Y (2007) Tetrahedron Lett 48:61 (Me2S+BrBr−)

    Google Scholar 

  25. Varala R, Nasreen A, Enugala R, Adapa SR (2007) Tetrahedron Lett 48:69 (L-Proline–CHCl3)

    Google Scholar 

  26. Ma H, Wang Y, Li J, Wang J (2007) Heterocycles 71:135 (Ionic liquid)

    Google Scholar 

  27. Nagawade RR, Shinde DB (2007) Indian J Chem 46B:349 (TiCl4)

    Google Scholar 

  28. Ramachary DB, Reddy GB (2006) Org Biomol Chem 4:4463 (L-Proline–EtOH)

  29. Ma H, Wang Y, Wang J (2006) Heterocycles 68:1669 (KHSO4)

  30. Lin S, Yang L (2005) Tetrahedron Lett 46:4315 (Dioxane-air)

  31. Curini M, Epifano F, Montanari F, Rosati O, Taccone S (2004) Synlett:1832 (Yb(OTf)3)

  32. Itoh T, Nagata K, Ishikawa H, Ohsawa A (2004) Heterocycles 63:2769 (Sc(OTf)3)

  33. Nagata K, Itoh T, Ishikawa H, Ohsawa A (2003) Heterocycles 61:93 (Sc(OTf)3)

  34. Beaulieu PL, Haché B, von Moos E (2003) Synthesis:1683 (Oxone®)

  35. Chakrabarty M, Mukherjee R, Karmakar S, Harigaya Y (2007) Monatsh Chem 138:1279

    Article  CAS  Google Scholar 

  36. Chakrabarty M, Mukherji A, Mukherjee R, Arima S, Harigaya Y (2007) Tetrahedron Lett 48:5239

    Article  CAS  Google Scholar 

  37. Chakrabarty M, Karmakar S, Mukherji A, Arima S, Harigaya Y (2006) Heterocycles 68:967

    Article  CAS  Google Scholar 

  38. Chakrabarty M, Kundu T, Arima S, Harigaya Y (2005) Tetrahedron Lett 46:2865

    Article  CAS  Google Scholar 

  39. Chakrabarty M, Ghosh N, Harigaya Y (2004) Tetrahedron Lett 45:4955

    Article  CAS  Google Scholar 

  40. Chakrabarty M, Sarkar S (2003) Tetrahedron Lett 44:8131

    Article  CAS  Google Scholar 

  41. Chakrabarty M, Sarkar S, Harigaya Y (2003) Synthesis:2292

  42. Breslow R, Maitra U, Rideout D (1983) Tetrahedron Lett 24:1901

    Article  CAS  Google Scholar 

  43. Rideout DC, Breslow R (1980) J Am Chem Soc 102:7816

    Article  CAS  Google Scholar 

  44. Makosza M (2000) Pure Appl Chem 72:1399

    Article  CAS  Google Scholar 

  45. Makosza M, Fedorynski M (1995) Handbook of phase transfer catalysis, In: Sasson Y, Neumann R (eds) Chapman & Hall, London

  46. Makosza M, Fedorynski M (1987) Adv Catal 35:375

    Article  CAS  Google Scholar 

  47. Ravi V, Ramu E, Vijay K, Rao AS (2007) Chem Pharm Bull 55:1254 (Zn(proline)2–H2O)

    Google Scholar 

  48. Salehi P, Dabiri M, Zolfigol MA, Otokesh S, Baghbanzadeh M (2006) Tetrahedron Lett 47:2557 (Silica sulfuric acid–LiCl-H2O)

  49. Bahrami K, Khodaei MM, Kavianinia I (2006) J Chem Res:783 (H2O2–HCl–LiCl–H2O, 100°C)

  50. Gogoi P, Konwar D (2006) Tetrahedron Lett 47:79 (I2–KI–K2CO3–H2O)

  51. Benson SC, Pershadsingh HA, Ho CI, Chittiboyina A, Desai P, Pravenec M, Qi N, Wang J, Avery MA, Kurtz TW (2004) Hypertension 43:993

    Article  CAS  Google Scholar 

  52. Spencer A (1985) J Organomet Chem 295:79

    Article  CAS  Google Scholar 

  53. Wolff L, Grun R, Kolasius F (1913) Ann 399:297

    CAS  Google Scholar 

  54. Navarrete-Vázquez G, Moreno-Diaz H, Estrada-Soto S, Torres-Piedra M (2007) Synth Commun 37:2815

    Article  CAS  Google Scholar 

  55. Sundberg RJ, Russell HF (1973) J Org Chem 38:3324

    Article  CAS  Google Scholar 

  56. Corey EJ, Chaykovsky M (1962) J Am Chem Soc 84:866

    Article  CAS  Google Scholar 

  57. Bellamy FD, Ou K (1984) Tetrahedron Lett 25:839

    Article  CAS  Google Scholar 

  58. Figge A, Altenbach HJ, Brauer DJ, Tielmann P (2002) Tetrahedron Asymmetry 13:137

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We sincerely thank Professor S. Raha, the Director, Bose Institute for laboratory facilities, the C.S.I.R., Government of India for providing a fellowship (S.K.), Mr. B. Majumder, NMR Facilities and Mr. P. Dey, Microanalytical Laboratory, both of the Bose Institute, for recording the spectra.

Author information

Authors and Affiliations

  1. Department of Chemistry, Bose Institute, 93/1, A. P. C. Road, Kolkata, 700009, India

    Manas Chakrabarty, Sulakshana Karmakar & Ratna Mukherjee

  2. School of Pharmaceutical Sciences, Kitasato University, Minato-ku, Tokyo, 108, Japan

    Shiho Arima & Yoshihiro Harigaya

Authors
  1. Manas Chakrabarty
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Sulakshana Karmakar
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ratna Mukherjee
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Shiho Arima
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Yoshihiro Harigaya
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Manas Chakrabarty.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Chakrabarty, M., Karmakar, S., Mukherjee, R. et al. A mild and expedient one-pot synthesis of substituted benzimidazoles in water using a phase-transfer catalyst. Monatsh Chem 140, 375–380 (2009). https://doi.org/10.1007/s00706-008-0036-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-008-0036-z

Keywords

Search

Navigation