Skip to main content
Log in

A simple route for the synthesis of novel \(N\)-alkyl-2-(alkylthio)-1\(H\)-imidazole derivatives

  • Short Communication
  • Published:
Molecular Diversity Aims and scope Submit manuscript

Abstract

Novel \(N\)-alkyl-2-(alkylthio)-1\(H\)-imidazole derivatives were synthesized in a single step by an efficient and simple method in high yields. Readily available starting materials, mild reaction conditions, operational simplicity and novelty are the key advantages of this method. Besides their novel structures, these compounds may have important biological activities and industrial applications.

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.

Fig. 1
Scheme 1
Fig. 2
Scheme 2
Scheme 3

References

  1. Bolani M, Gonzalez M (2005) Imidazole and benzimidazole derivatives as chemotherapeutic agents. Mini Rev Med Chem 5: 409–424. doi:10.2174/1389557053544047

    Google Scholar 

  2. Jin Z (2006) Imidazole, oxazole and thiazole alkaloids. Nat Prod Rep 23:464–496. doi:10.1039/B502166A

    Article  PubMed  CAS  Google Scholar 

  3. Saluja S, Zou R, Drach JC, Townsend LB (1996) Structure–activity relationships among 2-substituted 5,6-dichloro-, 4,6-dichloro-, and 4,5-dichloro-1-[(2-hydroxyethoxy)methyl]- and -1-[(1,3-dihydroxy-2-propoxy)methyl]benzimidazoles. J Med Chem 39:881–891. doi:10.1021/jm950556a

    Google Scholar 

  4. Tatsuta M, Kataoka M, Yasoshima K, Sakakibara S, Shogase Y, Shimazaki M, Yura T, Li Y, Yamamoto N, Guptab J, Urbahns K (2005) Benzimidazoles as non-peptide luteinizing hormone-releasing hormone (LHRH) antagonists. Part 3: discovery of 1-(1\(H\)-benzimidazol-5-yl)-3- \(tert\)-butylurea derivatives. Bioorg Med Chem Lett 15:2265–2269. doi: 10.1016/j.bmcl.2005.03.030

    Article  PubMed  CAS  Google Scholar 

  5. Jill A, Jablonowski KS, Ly MB, Curt AD, Jamin DB, Lisa KD, Brian L, Kirsten LM, Curt M, Sandy JW, Timothy WL, Nicholas IC (2009) Novel imidazole-based histamine \(\text{ H}_{3}\) antagonists. Bioorg Med Chem Lett 19:903–907. doi: 10.1016/j.bmcl.2008.11.114

    Article  Google Scholar 

  6. Fitton A, Wiseman L (1996) Pantoprazole: a review of its pharmaceutical properties and therapeutic use in acid-related disorders. Drugs 51:460–482

    Article  PubMed  CAS  Google Scholar 

  7. Barradell LB, Faulds D (1992) Lansoprazole: a review of its pharmacodynamic and pharmacokinetic properties and its therapeutic efficacy in acid-related disorders. Drugs 44:225–250

    Article  PubMed  CAS  Google Scholar 

  8. Mc Tavish D, Buckley MMT, Heel RC (1991) Omeprazole: an update review of its pharmacology and therapeutic use in acid related disorders. Drugs 42:138–170

    Article  CAS  Google Scholar 

  9. Delamare M, Belot S, Caille JC, Martinet F, Kagan HB, Henryon V (2009) A new titanate/(+)-(1\(R\),2\(S\))-\(cis\)-1-amino-2-indanol system for the asymmetric synthesis of (\(S\))-tenatoprazole. Tetrahedron Lett 50:1702–1704. doi: 10.1016/j.tetlet.2009.01.111

    Article  CAS  Google Scholar 

  10. Grimmett MR (1997) Imidazole and benzimidazole synthesis. Academic Press, Inc., San Diego, CA

    Google Scholar 

  11. Kamijo S, Yamamoto Y (2007) Recent progress in the catalytic synthesis of imidazoles. Chem Asian J 2:568–578. doi:10.1002/asia.200600418

    Article  PubMed  CAS  Google Scholar 

  12. Karimi AR, Alimohammadi Z, Amini MM (2010) Wells-Dawson heteropolyacid supported on silica: a highly efficient catalyst for synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles. Mol Divers 14:635–641. doi:10.1007/s11030-009-9197-x

    Article  PubMed  CAS  Google Scholar 

  13. Bellina F, Cauteruccio S, Rossi R (2007) Synthesis and biological activity of vicinal diaryl-substituted \(1H\)-imidazoles. Tetrahedron 63:4571–4624. doi:10.1016/j.tet.2007.02.075

    Google Scholar 

  14. Ermolat’ev DS, Savaliya B, Shah A, Van der Eycken E (2011) One-pot microwave-assisted protocol for the synthesis of substituted 2-amino-1\(H\)-imidazoles. Mol Divers 15:491–496. doi:10.1007/s11030-010-9270-5

    Google Scholar 

  15. Kianmehr E, Ghanbari M, Faramarzi R (2010) Novel one- pot three component reaction for the synthesis of [2-(alkylsulfanyl)imidazo[1,2-\(a\)]pyridin-3-yl](aryl)methanone. J Comb Chem 12:41–44. doi:10.1021/cc900103r

    Google Scholar 

  16. Kianmehr E, Rajabi A, Ghanbari M (2009) Palladium-catalyzed addition of arylboronic acids to isocyanates. Tetrahedron Lett 50:1687–1688. doi:10.1016/j.tetlet.2009.01.054

    Article  CAS  Google Scholar 

  17. Kianmehr E, Ghanbari M (2012) A direct palladium-catalyzed route for the synthesis of benzo\([a]\)carbazoles through Sequential C–C bond formation and C–H bond functionalization. Eur J Org Chem 256–259: doi:10.1002/ejoc.201101401

  18. Kianmehr E, Ghanbari M, Faghih N, Rominger F (2012) A palladium-catalyzed one-pot procedure for the regioselective dimerization and cyanation of indoles. Tetrahedron Lett 53: 1900–1904. doi:10.1016/j.tetlet.2012.01.129

  19. Cheng M, Hanfeng D, Yanguang W (2006) Novel annulation reactions of aryl methyl ketenes with zwitterions derived from dimethyl acetylenedicarboxylate and \(N\)-alkylimidazoles. Org Lett 8: 3133–3136. doi:10.1021/ol061126p

    Google Scholar 

  20. Adib M, Sheibani E, Mostofi M, Ghanbary K, Bijanzadeh HR (2006) Efficient highly diastereoselective synthesis of 1,8\(a\)-dihydro-7\(H\)-imidazo[2,1-\(b\)][1,3]oxazines. Tetrahedron 62:3435–3438. doi:10.1016/j.tet.2006.01.048

    Google Scholar 

Download references

Acknowledgments

We gratefully acknowledge the financial support from the Research Council of the University of Tehran.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Ebrahim Kianmehr.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (doc 13359 KB)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kianmehr, E., Shamsaei Zafarghandi, N. & Ghanbari, M. A simple route for the synthesis of novel \(N\)-alkyl-2-(alkylthio)-1\(H\)-imidazole derivatives. Mol Divers 17, 383–388 (2013). https://doi.org/10.1007/s11030-013-9430-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11030-013-9430-5

Keywords

Navigation