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Fe(ClO4)3· 6H2O: a mild and efficient catalyst for one-pot three component synthesis of β-acetamido carbonyl compounds under solvent-free conditions

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Abstract

A one-pot multi-component reaction for the synthesis of β-acetamido carbonyl compounds is reported. The reaction uses a variety of aldehydes, acetophenone derivatives or methyl acetoacetate, acetonitrile, and acetyl chloride in the presence of ferric perchlorate, a mild, efficient and inexpensive catalyst effective under solvent free conditions.

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References

  1. Terret NK, Gardner M, Gordon DW, Kobylecki RJ, Steele J (1995) Combinatorial synthesis—the design of compound libraries and their application to drug discovery. Tetrahedron 51: 8135–8173

    Article  Google Scholar 

  2. Armstrong RW, Combs AP, Tempest PA, Brown SD, Keating TA (1996) Multiple-component condensation strategies for combinatorial library synthesis. Acc Chem Res 29: 123–131

    Article  CAS  Google Scholar 

  3. Thomson LA, Ellman JA (1996) Synthesis and applications of small molecule libraries. Chem Rev 96: 555–600

    Article  Google Scholar 

  4. Dömling A, Ugi I (2000) Multicomponent reactions with isocyanides. Angew Chem Int Ed 39: 3168–3210

    Article  Google Scholar 

  5. Barluenga J, Viado AL, Aguilar E, Fustero S, Olano B (1993) 1,3-Amino alcohols from 4-amino-1-aza dienes. Diastereo and enantioselective approach to the four diastereoisomers of the N-terminal amino acid component of nikkomycins B and BX. J Org Chem 58: 5972–5975

    Article  CAS  Google Scholar 

  6. Enders D, Moser M, Geibel G, Laufer MC (2004) Diastereo and enantioselective synthesis of differently N,O-protected 1,3-amino alcohols with three neighbouring stereogenic centers. Synthesis 2040–2046

  7. Kobinata K, Uramoto M, Nishii M, Kusakabe H, Nakamura G, Isono K (1980) Neopolyoxins A, B, and C, new chitin synthetase inhibitors. Agric Biol Chem 44: 1709–1711

    CAS  Google Scholar 

  8. Dähn U, Hagenmaier H, Höhne H, König WA, Wolf G, Zähner H (1976) Stoffwechselprodukte von mikroorganismen. 154. Mitteilung. Nikkomycin, ein neuer hemmstoff der chitinsynthese bei pilzen. Arch Microbiol 107: 143–160

    Article  PubMed  Google Scholar 

  9. Mukhopadhyay M, Bhatia B, Iqbal J (1997) Cobalt catalyzed multiple component condensation route to β-acetamido carbonyl compound libraries. Tetrahedron Lett 38: 1083–1086

    Article  CAS  Google Scholar 

  10. Bhatia B, Reddy MM, Iqbal J (1994) Cobalt-catalysed three-component coupling involving ketones or ketoesters, aldehydes and acetonitrile: A novel one-pot synthesis of b-acetamido ketones. J Chem Soc Chem Commun 713–715

  11. Bahulayan D, Das SK, Iqbal J (2003) Montmorillonite K10 clay: an efficient catalyst for the one-pot stereoselective synthesis of β-acetamido ketones. J Org Chem 68: 5735–5738

    Article  PubMed  CAS  Google Scholar 

  12. Khodaei MM, Khosropour AR, Fattahpour P (2005) 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 46: 2105–2108

    Article  CAS  Google Scholar 

  13. Ghosh R, Maity S, Chakraborty A (2005) One-pot multicomponent synthesis of β-acetamido ketones based on BiCl3 generated in situ from the procatalyst BiOCl and acetyl chloride. Synlett 115–118

  14. Ghosh R, Maity S, Chakraborty A, Chakraborty S, Mukherjee AK (2006) ZrOCl 2· 8H 2O: an efficient Lewis acid catalyst for the one-pot multicomponent synthesis of β-acetamido ketones. Tetrahedron 62: 4059–4064

    Article  CAS  Google Scholar 

  15. Rafiee E, Tork F, Joshaghani M (2006) Heteropoly acids as solid green Brønsted acids for a one-pot synthesis of β-acetamido ketones by Dakin–West reaction. Bioorg Med Chem Lett 16: 1221–1226

    Article  PubMed  CAS  Google Scholar 

  16. Yakaiah T, Reddy G, Lingaiah BPV, Narsaiah B, Rao PS (2005) Silica sulfuric acid: an efficient and recyclable catalyst for the synthesis of β-acetamido ketones in single pot. Synth Commun 35: 1307–1312

    Article  CAS  Google Scholar 

  17. Pandey G, Singh RP, Garg A, Singh VK (2005) Synthesis of Mannich type products via a three-component coupling reaction. Tetrahedron Lett 46: 2137–2140

    Article  CAS  Google Scholar 

  18. Rafiee E, Shahbazi F, Joshaghani M, Tork F (2005) 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 242: 129–134

    Article  CAS  Google Scholar 

  19. Heravi MM, Ranjbar L, Derikvand F, Bamoharram FF (2007) H6P2W18O62: an efficient and reusable catalyst for one-pot synthesis of β-acetamido ketone and esters. Catal Commun 8: 289–291

    Article  CAS  Google Scholar 

  20. Khan AT, Parvin T, Choudhury LH (2007) Iron(III) chloride-catalyzed convenient one-pot synthesis of β-acetamido carbonyl compounds. Tetrahedron 63: 5593–5601

    Article  CAS  Google Scholar 

  21. Heravi MM, Behbahani FK, Oskooie HA, Shoar RH (2005) Mild and efficient tetrahydropyranylation of alcohols and dehydropyranylation of THP ethers catalyzed by ferric perchlorate. Tetrahedron Lett 46: 2543–2545

    Article  CAS  Google Scholar 

  22. Heravi MM, Behbahani FK, Oskooie HA, Shoar RH (2006) Catalytic acetylation of alcohols and phenols with ferric perchlorate in acetic acid. Catal Commun 7: 136–139

    Article  CAS  Google Scholar 

  23. Heravi MM, Behbahani FK, Oskooie HA, Shoar RH (2005) Catalytic aromatization of Hantzsch 1,4-dihydropyridines by ferric perchlorate in acetic acid. Tetrahedron Lett 46: 2775–2777

    Article  CAS  Google Scholar 

  24. Heravi MM, Zadsirjan V, Behbahani FK, Oskooie HA (2006) Catalytic synthesis of 2,3-dihydro-1H-1,5-benzodiazepines by ferric perchlorate. J Mol Catal A: Chem 259: 201–204

    Article  CAS  Google Scholar 

  25. Heravi MM, Behbahani FK, Shoar RH, Oskooie HA (2006) Ferric perchlorate: a novel and highly efficient catalyst for direct acetylation of THP ethers with acetic acid. J Mol Catal A: Chem 244: 8–10

    Article  CAS  Google Scholar 

  26. Oskooie HA, Heravi MM, Sadnia A, Safarzadegan M, Behbahani FK (2007) Mild and efficient conversion of oximes into arylhydrazones catalysed by ferric perchlorate. Mendeleev Commun 17: 190–191

    Article  CAS  Google Scholar 

  27. Oskooie HA, Heravi MM, Sadnia A, Jannati F, Behbahani FK (2007) Ferric perchlorate—catalyzed one-pot synthesis of alpha aminonitriles using trimethylsilylcyanide. Synthetic Commun 37: 2543–2548

    Article  CAS  Google Scholar 

  28. Oskooie HA, Heravi MM, Sadnia A, Behbahani FK, Jannati F (2007) Solventless synthesis of 2-aryl-1-arylmethyl-1H-1,3-benzimidazoles catalyzed by Fe(ClO4)3 at room temperature. Chinese Chem Lett 18: 1357–1360

    CAS  Google Scholar 

  29. Rao IN, Prabhakaran EN, Das SK, Iqbal J (2003) Cobalt-catalyzed one-pot three-component coupling route to b-acetamido carbonyl compounds: A general synthetic protocol for c-lactams. J Org Chem 68: 4079–4082

    Article  PubMed  CAS  Google Scholar 

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Correspondence to Majid M. Heravi.

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Heravi, M.M., Behbahani, F.K., Daraie, M. et al. Fe(ClO4)3· 6H2O: a mild and efficient catalyst for one-pot three component synthesis of β-acetamido carbonyl compounds under solvent-free conditions. Mol Divers 13, 375–378 (2009). https://doi.org/10.1007/s11030-009-9118-z

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  • DOI: https://doi.org/10.1007/s11030-009-9118-z

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