Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 21
202
Views
11
CrossRef citations to date
0
Altmetric
Original Articles

Silica-Supported Perchloric Acid (HClO4-SiO2): An Efficient Catalyst for the Preparation of β-Amido Carbonyl Compounds Using Multicomponent Reactions

, &
Pages 3766-3777 | Received 24 Apr 2008, Published online: 14 Oct 2008

REFERENCES

  • (a) Zhu , J. ; Bienayme , H. (Eds). Multicomponent Reactions ; Wiley : Weinheim , 2005 ; (b) Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. A. Multiple-component condensation strategies for combinatorial library synthesis. Acc. Chem. Res. 1996, 29, 123–131; (c) Terret, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steel, J. Combinatorial synthesis—The design of compound libraries and their application to drug discovery. Tetrahedron 1995, 51, 8135–8173 .
  • Casimir , J. R. ; Turetta , C. ; Ettouati , L. ; Paris , J. First application of the Dakin–West reaction to fmoc chemistry: Synthesis of the ketomethylene tripeptide fmoc-Nα-Asp(tBu)-(R,S Tyr(tBu)Ψ(CO–CH)Gly-OH . Tetrahedron Lett. 1995 , 36 , 4797 – 4800 .
  • Godfrey , A. G. ; Brooks , D. A. ; Hay , L. A. ; Peters , M. ; McCarthy , J. R. ; Mitchell , D. Application of the Dakin–West reaction for the synthesis of oxazole-containing dual PPARα/γ agonists . J. Org. Chem. 2003 , 68 , 2623 – 2632 .
  • Dähn , U. ; Hagenmaier , H. ; Höhne , H. ; König , W.A. ; Wolf , G. ; Zähner , H. Stoffwechselprodukte von mikroorganismen. 154. Mitteilung. Nikkomycin, ein neuer hemmstoff der chitinsynthese bei pilzen . Arch. Microbiol. 1976 , 107 , 143 – 160 .
  • (a) Dakin , H. D. ; West , R. A general reaction of amino acids . J. Biol. Chem. 1928 , 78 , 745 – 756 ; (b) Dakin , H. D. ; West , R. A general reaction of amino acides (II) . J. Biol. Chem. 1928 , 78 , 91 – 104 ; (c) Dakin , H. D. ; West , R. Some aromatic derivatives of substituted acetylaminoacetones . J. Biol. Chem. 1928 , 78 , 757 – 764 ; (d) Buchanan , G. L. The Dakin–West reaction . Chem. Soc. Rev. 1988 , 17 , 91 – 111 .
  • Rao , I. N. ; Prabhakaran , E. N. ; Das , S. K. ; Iqbal , J. Cobalt-catalyzed one-pot three-component coupling route to β-acetamido carbonyl compounds: A general synthetic protocol for γ-lactams . J. Org. Chem. 2003 , 68 , 4079 – 4082 .
  • Bhatia , B. ; Reddy , M. M. ; Iqbal , J. Cobalt-catalysed three-component coupling involving ketones or ketoesters, aldehydes and acetonitrile: A novel one-pot synthesis of β-acetamido ketones. J. Chem. Soc. Chem. Commun. 1994, 713–715.
  • Bahulayan , D. ; Das , S. K. ; Iqbal , J. Montmorillonite K10 clay: An efficient catalyst for the one-pot stereoselective synthesis of β-acetamido ketones . J. Org. Chem. 2003 , 68 , 5735 – 5738 .
  • Khodaei , M. M. ; Khosropour , A. R. ; Fattahpour , P. A modified procedure for the Dakin–West reaction: An efficient and convenient method for a one-pot synthesis of β-acetamido ketones using silica sulfuric acid as catalyst . Tetrahedron Lett. 2005 , 46 , 2105 – 2108 .
  • Ghosh , R. ; Maity , S. ; Chakraborty , A. One-pot multicomponent synthesis of β-acetamido ketones based on BiCl3 generated in situ from the procatalyst BiOCl and acetyl chloride . Synlett 2005 , 115 – 118 .
  • Ghosh , R. ; Maity , S. ; Chakraborty , A. ; Chakraborty , S. ; Mukherjee , A. K. ZrOCl2·8H2O: An efficient Lewis acid catalyst for the one-pot multicomponent synthesis of β-acetamido ketones . Tetrahedron 2006 , 62 , 4059 – 4064 .
  • Rafiee , E. ; Tork , F. ; Joshaghani , M. Heteropoly acids as solid green Brønsted acids for a one-pot synthesis of β-acetamido ketones by Dakin–West reaction . Bioorg. Med. Chem. Lett. 2006 , 16 , 1221 – 1226 .
  • Rafiee , E. ; Shahbazi , F. ; Joshaghani , M. ; Tork , F. The silica supported H3PW12O40 (a heteropoly acid) as an efficient and reusable catalyst for a one-pot synthesis of β-acetamido ketones by Dakin–West reaction . J. Mol. Catal. A: Chem. 2005 , 242 , 129 – 134 .
  • Yakaiah , T. ; Reddy , V. G. ; Lingaiah , B. P. V. ; Narsaiah , B. ; Shanthan-Rao , P. Silica sulphuric acid: An efficient and recyclable catalyst for the synthesis of β-acetamido ketones in single pot . Synth. Commun. 2005 , 35 , 1307 – 1312 .
  • Pandey , G. ; Singh , R. P. ; Garg , A. ; Singh , V. K. Synthesis of Mannich type products via a three-component coupling reaction . Tetrahedron Lett. 2005 , 46 , 2137 – 2140 .
  • Nagarapu , L. ; Kantevari , S. ; Cheemalapati , V. N. ; Apuri , S. ; Kumari , V. Potassium dodecatungstocobaltate trihydrate (K5CoW12O40·3H2O): A mild and efficient reusable catalyst for the synthesis of β-acetamido ketones under solvent-free conditions . J. Mol. Catal. A: Chem. 2007 , 264 , 22 – 25 .
  • Khan , A. T. ; Choudhury , L. H. ; Parvin , T. ; Asif-Ali , M. CeCl3·7H2O: An efficient and reusable catalyst for the preparation of β-acetamido carbonyl compounds by multi-component reactions (MCRs) . Tetrahedron Lett. 2006 , 47 , 8137 – 8141 .
  • Maghsoodlou , M. T. ; Hassankhani , A. ; Shaterian , H. R. ; Habibi-Khorasani , S. M. ; Mosaddegh , E. Zinc oxide as an economical and efficient catalyst for the one-pot preparation of β-acetamido ketones via a four-component condensation reaction . Tetrahedron Lett. 2007 , 48 , 1729 – 1734 .
  • Das , B. ; Reddy , K. R. ; Ramu , R. ; Thirupathi , P. ; Ravikanth , B. Iodine as an efficient catalyst for one-pot multicomponent synthesis of β-acetamido ketones. Synlett 2006, 1756–1758.
  • Das , B. ; Reddy , K. R. Facile one-pot multicomponent synthesis of β-acetamido ketones with amberlyst-15 as heterogeneous catalyst . Helv. Chim. Acta. 2006 , 89 , 3109 – 3111 .
  • Das , B. ; Krishnaiah , M. ; Laxminarayana , K. ; Reddy , K. R. A simple and efficient one-pot synthesis of β-acetamido carbonyl compounds using sulfated zirconia as a heterogeneous recyclable catalyst . J. Mol. Catal. A: Chem. 2007 , 270 , 284 – 288 .
  • Khan , A. ; Parvin , T. ; Choudhury , L. H. Iron(III) chloride-catalyzed convenient one-pot synthesis of β-acetamido carbonyl compounds . Tetrahedron 2007 , 63 , 5593 – 5601 .
  • Das , B. ; Reddy , K. R. ; Srinivas , Y. ; Kumar , R. A. One-pot multicomponent synthesis of β-acetamidoketones catalysed by p-TSA . Can. J. Chem. 2007 , 85 , 479 – 482 .
  • Shaterian , H. R. ; Hosseinian , A. ; Ghashang , M. One-pot preparation of β-amido ketones/esters in three-component condensation reaction using magnesium hydrogensulfate as effective and reusable catalyst . Can. J. Chem. 2008 , 86 , 376 – 383 .
  • Shaterian , H. R. ; Yarahmadi , H. ; Ghashang , M. One-pot preparation of β-amido ketones and esters in four-component condensation reaction using ferric hydrogensulfate as effective and reusable catalyst . Arkivoc 2007 , 16 , 298 – 313 .
  • Mirjafary , Z. ; Saeidian , H. ; Sadeghi , A. ; Moghaddam , F. M. ZnO nanoparticles: An efficient nanocatalyst for the synthesis of β-acetamido ketones/esters via a multi-component reaction . Catal. Commun. 2008 , 9 , 299 – 306 .
  • Anastas , P. T. Green Chemistry Theory and Practice ; Oxford University Press : Oxford , 2000 .
  • Shaterian , H. R. ; Shahrekipoor , F. ; Ghashang , M. Silica supported perchloric acid (HClO4–SiO2): A highly efficient and reusable catalyst for the protection of hydroxyl groups using HMDS under mild and ambient conditions . J. Mol. Catal. A: Chem. 2007 , 272 , 142 – 151 .
  • Chakraborti , A. K. ; Gulhane , R. Perchloric acid adsorbed on silica gel as a new, highly efficient, and versatile catalyst for acetylation of phenols, thiols, alcohols, and amines . Chem. Commun. 2003 , 1896 – 1897 ; Chakraborti, A. K.; Gulhane, R. Indian Patent 266/DEL/2003, March 10, 2003 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.