Skip to main content
Log in

SBA-15-Pr–SO3H: An efficient, environment friendly and recyclable heterogeneous nanoreactor catalyst for the one-pot multicomponent synthesis of β-acetamido ketones

  • Published:
Journal of Chemical Sciences Aims and scope Submit manuscript

Abstract

SBA-15-Pr–SO3H catalyzes the multi-component condensation of aromatic aldehydes, ketones and acetonitrile in the presence of acetyl chloride at 80°C to afford β-acetamido ketones in excellent yields. The catalyst can be recovered and recycled for subsequent reactions without any appreciable loss of efficiency.

SBA-15-Pr–SO3H as nanoreactor catalyzes the multicomponent condensation of aromatic aldehydes, ketones, and acetonitrile in the presence of acetyl chloride at 80°C to afford β-acetamido ketones in excellent yields.

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
Figure 2
Figure 3
Scheme 1
Scheme 2
Scheme 3

Similar content being viewed by others

References

  1. (a) Terret N K, Gardner M, Gordon D W, Kobylecki, R J and Steele J 1995 Tetrahedron 51 8135; (b) Armstrong R W, Combs A P, Tempest P A, Brown S D and Keating T A 1996 Acc. Chem. Res. 29 123; (c) Thomson L A and Ellman J A 1996 Chem. Rev. 96 555; (d) Tietze L F and Lieb M E 1998 Curr. Opin. Chem. Biol. 2 363; (e) Domling A and Ugi I 2000 Angew. Chem. Int. Ed. 39 3168

  2. Casimir J R, Turetta C, Ettouati L and Paris J 1995 Tetrehedron Lett. 36 4797

  3. Godfrey A G, Brooks D A, Hay L A, Peters M, McCarthy J R and Mitchell D 2003 J. Org. Chem. 68 2623

  4. Barluenga J, Viado A L, Aguilar E, Fustero S and Olano B 1993 J. Org. Chem. 58 5972

  5. Enders D, Moser M, Geibel G and Laufer M C 2004 Synthesis 2040

  6. Dahn U, Hagenmaier H, Hohne H, Konig W A, Wolf G and Zahner H 1976 Arch. Microbiol. 107

  7. Kobinata K, Uramoto M, Nishii M, Kusakabe H, Nakamura G and Isono K 1980 Agric. Biol. Chem. 44 1709

  8. (a) Mukhopadhyay M, Bhatiaand B and Iqbal J 1997 Tetrahedron Lett. 38 1083; (b) Khan A T, Parvin T and Choudhury L H 2007 Tetrahedron 63 5593

  9. (a) Bahulayan D, Das S K and Iqbal J 2003 J. Org. Chem. 68 5735; (b) Shinu V S, Sheeja B, Purushothaman E and Bahulayan D 2009 Tetrahedron Lett. 50 4838

  10. (a) Khodaei M M, Khosropour A R and Fattahpour P 2005 Tetrahedron Lett. 46 2105; (b) Khan A T, Choudhury L H, Parvin T and Ali M A 2006 Tetrahedron Lett. 47 8137

  11. (a) Pandey G, Singh R P, Garg A and Singh V K 2005 Tetrahedron Lett. 46 2137; (b) Mao H, Wan J and Pan Y 2009 Tetrahedron 65 1026

  12. (a) Gholivand K, Jafari H and Adibi H 2011 Synth. Commun. 41 1786; (b) Bhat R P, Vivek P R, Varghese M A, Sachin B P and Samant S D 2005 Tetrahedron Lett. 46 4801; (c) Das B, Reddy K R, Ramu R, Thirupathi P and Ravikanth B 2006 Synlett 1756

  13. (a) Corma A 1997 Chem. Rev. 97 2373; (b) Karimi B and Vafaeezadeh M 2012 Chem. Commun. 48 3327

  14. Li C 2004 Catal. Rev. 46 419

  15. Taguchi A and Schuth F 2005 Microporous Mesoporous Mater. 77 1

  16. Zhao X S, Bao X Y, Guo W P and Lee F Y 2006 Mater. Today 9 32

  17. Wang Y J and Caruso F 2005 Chem. Mater. 17 953

  18. (a) Liu C J, Li S J, Pang W Q and Che C M 1997 Chem. Commun. 65; (b) Kresge C T, Leonowicz M E, Roth W J, Vartuli J C and Beck J S 1992 Nature 359 710; (c) Lin V S-Y, Radu D R, Han M K, Deng W, Kuroki S, Shanks B H and Pruski M 2002 J. Am. Chem. Soc. 124 9040

  19. Yang L M, Wang Y J, Luo G S and Dai Y Y 2005 Microporous Mesoporous Mater. 84 275

  20. Bahrami K, Khodaei M M and Abbasi J 2012 Synthesis 316

  21. Bahrami K, Khodaei M M and Fattahpour P 2011 Catal. Sci. Technol. 1 389

  22. Bhatia B, Reddy M M and Iqbal J 1994 J. Chem. Res. (S) 713

  23. Maiti S and Chakraborty A 2005 Synlett 115

  24. Kumar A, Rao M S, Ahmad I and Khungar B 2009 Aust. J. Chem. 62 322

  25. (a) Rafiee E, Tork F and Johaghani M 2006 Bioorg. Med. Chem. Lett. 16 1221; (b) Yakaiah T, Lingaiah, B P V, Reddy G V, Narsaiah B and Rao P S 2007 Arkivoc viii 227; (c) Momeni A R and Sadeghi M 2009 Appl. Catal. A: Gen. 357 100

  26. Rafiee E, Shahbazi F, Joshaghani M and Tork F 2005 J. Mol. Catal. A: Chem. 242 129

  27. Selvam N P and Perumal P T 2007 Arkivoc 10 265

  28. Maghsoodlou M T, Hassankhani A, Shaterian H R, Habibi-Khorasani S M and Mosaddegh E 2007 Tetrahedron Lett. 48 1729

  29. Tayebee R and Taizabi S 2011 Am. J. Chem. 1 22

  30. Shaterian H R, Hosseinian A and Ghashang M 2008 Synth. Commun. 38 3766

Download references

Acknowledgments

We are thankful to the Razi University Research Council for partial support of this work.

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to KIUMARS BAHRAMI or MOHAMMAD M KHODAEI.

Additional information

Supplementary Information

Complete experimental procedures and relevant spectra (1H NMR and 13C NMR spectra) for some compounds (figure S1S8) are given in Supplementary Information, which is available free of charge in www.ias.ac.in/chemsci.

Electronic supplementary material

Below is the link to the electronic supplementary material.

(DOC 758 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

BAHRAMI, K., KHODAEI, M.M. & FATTAHPOUR, P. SBA-15-Pr–SO3H: An efficient, environment friendly and recyclable heterogeneous nanoreactor catalyst for the one-pot multicomponent synthesis of β-acetamido ketones. J Chem Sci 127, 167–172 (2015). https://doi.org/10.1007/s12039-014-0762-1

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12039-014-0762-1

Keywords

Navigation