Skip to main content
SpringerLink
Log in

Nano-TiCl4/SiO2: an efficient catalyst for the one-pot synthesis of highly substituted dihydro-2-oxopyrroles

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

Abstract

Nano-TiCl4/SiO2 was used as a readily available, inexpensive, efficient, and environmentally benign heterogeneous solid acid catalyst for the one-pot cascade synthesis of highly functionalized dihydro-2-oxopyrroles. Four-component reaction (4CR) of dialkyl acetylenedicarboxylates, aniline derivatives, and formaldehyde was employed for the synthesis of these compounds under thermal conditions.

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

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Gao X, Cui Y, Levenson RM, Chung LWK, Nie S (2004) Nat Biotech 22:969

    Article  CAS  Google Scholar 

  2. Whitesides GM (2003) Nat Biotech 21:1161

    Article  CAS  Google Scholar 

  3. Michalet X, Pinaud FF, Bentolila LA, Tsay JM, Doose S, Li JJ (2005) Science 307:538

    Article  CAS  Google Scholar 

  4. Niemeyer CM (2001) Angew Chem Int Ed 40:4128

    Article  CAS  Google Scholar 

  5. Otsuka H, Nagasaki Y, Kataoka K (2003) Adv Drug Deliv Rev 55:403

    Article  CAS  Google Scholar 

  6. Petkar KC, Chavhan SS, Agatonovik-Kustrin S, Sawant KK (2011) Crit Rev Ther Drug Carrier Syst 28:101

    Article  CAS  Google Scholar 

  7. Ochekpe NA, Olorunfemi PO, Ngwuluka NC (2009) Trop J Pharm Res 8:275

    CAS  Google Scholar 

  8. Matthews L, Kanwar RK, Zhou S, Punj V, Kanwar JR (2010) The Open Trop Med J 3:1

    CAS  Google Scholar 

  9. Xiaolan S, Hongyan LIU, Haiping Y, Xiaowei Z, Dayu XU, Guanzhou QIU (2008) J Chin Ceram Soc 8:34

    Google Scholar 

  10. Tang S, Zou P, Xiong H, Tang H (2008) Carbohyd Polym 72:521

    Article  CAS  Google Scholar 

  11. Qian J, He P, Nie K (2004) J Appl Polym Sci 91:1013

    Article  CAS  Google Scholar 

  12. Zhang X, Xu W, Xia X, Zhang Z, Yu R (2006) Mater Lett 60:3319

    Article  CAS  Google Scholar 

  13. Yang H, Zhu Y (2005) Anal Chim Acta 554:92

    Article  CAS  Google Scholar 

  14. Kalinski C, Lemoine H, Schmidt J, Burdack C, Kolb J, Umkehrer M (2008) Synthesis 4007

  15. Landquist JK (1984) Application as pharmaceuticals. In: Katritzky AR, Rees CW (eds) Comprehensive Heterocyclic Chemistry, vol 1. Pergamon Press, New York, p 143

    Chapter  Google Scholar 

  16. Crowley PJ (1984) In: Katritzky AR, Rees CW (eds) Comprehensive Heterocyclic Chemistry, vol 1. Pergamon Press, New York, p 185

    Chapter  Google Scholar 

  17. Hinio TK, Machida TG, Hino AK, Oume AY, Hachioji HM (1990) Herbicidally active 2,5-dihydropyrroles. US Patent 4,909,828, Mar 20, 1990. Chem Abstr 112:198388

    Google Scholar 

  18. Tarnavsky SS, Dubinina GG, Golovach SM, Yarmoluk SM (2003) Biopolym Cell 19:548

    Article  Google Scholar 

  19. Boehner B, Baumann M (1980) Pesticidal 5-oxo-2,5 dihydropyrrole. US Patent 4,220,655, Sep 2, 1980. Chem Abstr 88:152415

    Google Scholar 

  20. Kawasuji T, Fuji M, Yoshinaga T, Sato A, Fujiwara T, Kiyama R (2007) Bioorg Med Chem 15:5487

    Article  CAS  Google Scholar 

  21. Demir AS, Aydogan F, Akhmedov IM (2002) Tetrahedron Asymmetry 13:601

    Article  CAS  Google Scholar 

  22. Feng Z, Li X, Zheng G, Huang L (2009) Bioorg Med Chem Lett 19:2112

    Article  CAS  Google Scholar 

  23. Singh SB, Goetz MA, Jones ET, Bills GF, Giacobbe RA, Herranz L, Stevens-Miles S, Williams DL Jr (1995) J Org Chem 60:7040

    Article  CAS  Google Scholar 

  24. He H, Yang HY, Bigelis R, Solum EH, Greenstein M, Carter GT (2002) Tetrahedron Lett 43:1633

    Article  CAS  Google Scholar 

  25. Suzuki S, Hosoe T, Nozawa K, Kawai K-I, Yaguchi T, Udagawa S-I (2000) J Nat Prod 63:768

    Article  CAS  Google Scholar 

  26. Clark AJ, Dell CP, McDonagh JM, Geden J, Mawdsley P (2003) Org Lett 5:2063

    Article  CAS  Google Scholar 

  27. Chen J, Huang PQ, Queneau Y (2009) J Org Chem 74:7457

    Article  CAS  Google Scholar 

  28. Alizadeh A, Mokhtari J, Zhu LG (2013) C R Chimie 16:863

    Article  CAS  Google Scholar 

  29. Zhu Q, Jiang H, Li J, Liu S, Xia C, Zhang M (2009) J Comb Chem 11:685

    Article  CAS  Google Scholar 

  30. Khan AT, Ghosh A, Musawwer Khan M (2012) Tetrahedron Lett 53:2622

    Article  CAS  Google Scholar 

  31. Zhu Q, Gao L, Chen Z, Zheng S, Shu H, Li J (2012) Eur J Med Chem 54:232

    Article  CAS  Google Scholar 

  32. Lv L, Zheng S, Cai X, Chen Z, Zhu Q, Liu S (2013) ACS Comb Sci 15:183

    Article  CAS  Google Scholar 

  33. Rana S, Brown M, Dutta A, Bhaumik A, Mukhopadhyay C (2013) Tetrahedron Lett 54:1371

    Article  CAS  Google Scholar 

  34. Sajadikhah S, Hazeri N (2014) Res Chem Intermed 40:737

    Article  CAS  Google Scholar 

  35. Sajadikhah S, Hazeri N, Maghsoodlou M, Habibi-Khorassani S, Beigbabaei A, Willis A (2013) J Iran Chem Soc 10:863

    Article  CAS  Google Scholar 

  36. Sajadikhah SS, Maghsoodlou MT, Hazeri N (2014) Chin Chem Lett 25:58

    Article  CAS  Google Scholar 

  37. Mirjalili BBF, Zamani L (2014) South Afr J Chem 67:21

    CAS  Google Scholar 

  38. Mirjalili BBF, Bamoniri A, Zamani L (2012) Lett Org Chem 9:338

    Article  CAS  Google Scholar 

  39. Zeitler VA, Brown CA (1957) J Phys Chem 61:1174

    Article  CAS  Google Scholar 

  40. Schrijnemakers K, Pascal VDV, Vansant EF (1999) Phys Chem Chem Phys 1:2569

    Article  CAS  Google Scholar 

  41. Jenkins R, Synder RL (1996) Introduction to x-ray powder diffractometry. John Wiley & Sons, New York

    Book  Google Scholar 

Download references

Acknowledgments

The authors are grateful to the University of Kashan for provising support to this work by Grant No. 159148/30.

Author information

Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan, Islamic Republic of Iran

    Abdolhamid Bamoniri & Reza Tarazian

  2. Department of Chemistry, College of Science, Yazd University, Yazd, Islamic Republic of Iran

    Bi Bi Fatemeh Mirjlili

Authors
  1. Abdolhamid Bamoniri
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Bi Bi Fatemeh Mirjlili
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Reza Tarazian
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Abdolhamid Bamoniri.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (PDF 4315 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Bamoniri, A., Mirjlili, B.B.F. & Tarazian, R. Nano-TiCl4/SiO2: an efficient catalyst for the one-pot synthesis of highly substituted dihydro-2-oxopyrroles. Monatsh Chem 146, 2107–2115 (2015). https://doi.org/10.1007/s00706-015-1481-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-015-1481-0

Keywords

Search

Navigation