Skip to main content
Log in

An ionic liquid as reaction medium for the synthesis of halo-containing β-enaminones at room temperature

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

Abstract

A series of twenty halomethylated β-enaminones [RC(O)CH=C(R 1)NR 3 R 4, where R = CF3,CCl3, CHCl2; R 1 = H, Me, Ph; R 3 = H, Me, Bu, Et; R 4 = Me, Et, Bu, allyl, tert-amyl, CH2CH2OH, Bn, Ph] were synthesized using the ionic liquid [bmim]BF4 at room temperature. It is demonstrated that this ionic liquid is a reaction medium suitable for the amination of β-alkoxyvinyl halomethyl ketones. The advantages of this method are the absence of solvents, short reaction times, and good 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.

Similar content being viewed by others

References

  • MAP Martins W Cunico CMP Pereira AFC Flores HG Bonacorso N Zanatta (2004) Curr Org Synthesis 1 391 Occurrence Handle10.2174/1570179043366611 Occurrence Handle1:CAS:528:DC%2BD2cXnsFGjt7s%3D

    Article  CAS  Google Scholar 

  • A Laurent J Diab IL Dréan (1997) J Fluorine Chem 84 145 Occurrence Handle10.1016/S0022-1139(97)00056-0

    Article  Google Scholar 

  • JC Sloop CL Bumgardner WD Loehle (2002) J Fluorine Chem 118 135 Occurrence Handle10.1016/S0022-1139(02)00221-X Occurrence Handle1:CAS:528:DC%2BD38Xosl2jtbs%3D

    Article  CAS  Google Scholar 

  • HG Bonacorso AP Wentz RV Lourega CA Cechinel TS Moraes HS Coelho N Zanatta MAP Martins M Hörner SH Alves (2006) J Fluorine Chem 12 1066 Occurrence Handle10.1016/j.jfluchem.2006.05.005

    Article  Google Scholar 

  • K Chroust M Pavlová Z Prokop J Mendel K Božková Z Kubát V Zajičková J Damborský (2007) Chemosphere 67 152 Occurrence Handle10.1016/j.chemosphere.2006.09.020 Occurrence Handle1:CAS:528:DC%2BD2sXnslKquw%3D%3D

    Article  CAS  Google Scholar 

  • Lyle FR (1985) US Patent 5 973 257

  • FR Lyle (1985) Chem Abstr 65 2870

    Google Scholar 

  • F Epifano S Genovese M Curini (2007) Tetrahedron Lett 48 2717 Occurrence Handle10.1016/j.tetlet.2007.02.064 Occurrence Handle1:CAS:528:DC%2BD2sXjtVWqurc%3D

    Article  CAS  Google Scholar 

  • J Lin L-F Zhang (2007) Monatsh Chem 138 77 Occurrence Handle10.1007/s00706-006-0565-2 Occurrence Handle1:CAS:528:DC%2BD2sXksl2k

    Article  CAS  Google Scholar 

  • AR Gholap NS Chakor T Daniel RJ Lahoti KV Srinivasan (2006) J Mol Catal A: Chem 245 37 Occurrence Handle10.1016/j.molcata.2005.09.021 Occurrence Handle1:CAS:528:DC%2BD28XhtFGrsb4%3D

    Article  CAS  Google Scholar 

  • Z-H Zhang J-Y Hu (2006) J Braz Chem Soc 17 1447 Occurrence Handle1:CAS:528:DC%2BD28XhtlWksLnN

    CAS  Google Scholar 

  • NV Lyutenko II Gerus AD Kacharov VP Kukhar (2003) Tetrahedron 59 1731 Occurrence Handle10.1016/S0040-4020(03)00106-6 Occurrence Handle1:CAS:528:DC%2BD3sXht1yqtLk%3D

    Article  CAS  Google Scholar 

  • J-T Liu X-J Yang F-L Zhao (2004) J Fluorine Chem 125 415 Occurrence Handle10.1016/j.jfluchem.2004.03.006

    Article  Google Scholar 

  • B Das K Venkateswarlu A Majhi MR Reddy KN Reddy YK Rao K Ravikumar B Sridhar (2006) J Mol Catal A: Chem 246 276 Occurrence Handle10.1016/j.molcata.2005.11.045 Occurrence Handle1:CAS:528:DC%2BD28Xhslequrg%3D

    Article  CAS  Google Scholar 

  • M Hojo R Masuda SS Okada H Narumiya K Marimoto (1989) Tetrahedron Lett 30 6173 Occurrence Handle10.1016/S0040-4039(01)93334-9 Occurrence Handle1:CAS:528:DyaK3cXitlCkt70%3D

    Article  CAS  Google Scholar 

  • N Zanatta DC Flores SS Amaral HG Bonacorso MAP Martins AFC Flores (2005) Synlett 20 3079 Occurrence Handle10.1055/s-2005-922747

    Article  Google Scholar 

  • Zanatta N, Squizani AMC, Fantinel L, Nachtigall FM, Bonacorso HB, Martins MAP (2002) Synthesis:2409

  • MAP Martins RL Peres GF Fiss FA Dimer R Mayer CP Frizzo MRB Marzari N Zanatta HG Bonacorso (2007) J Braz Chem Soc 18 1486 Occurrence Handle1:CAS:528:DC%2BD1cXhvFeisLc%3D

    CAS  Google Scholar 

  • MAP Martins CMP Pereira W Cunico S Moura FA Rosa RL Peres P Machado N Zanatta HG Bonacorso (2006) Ultrason Sonochem 13 364 Occurrence Handle1:CAS:528:DC%2BD28XjtFGru7s%3D

    CAS  Google Scholar 

  • MAP Martins W Cunico S Brondani RL Peres N Zimmermann FA Rosa GF Fiss N Zanatta HG Bonacorso (2006) Synthesis 9 1485 Occurrence Handle10.1055/s-2006-926443

    Article  Google Scholar 

  • Martins MAP, Frizzo CP, Moreira DN, Rosa FA, Marzari MRB, Zanatta N, Bonacorso HG (2007) Catal Commun, doi: 10.1016/j.catcom.2007.11.037

  • MAP Martins EA Guarda CP Frizzo E Scapin P Beck AC Costa N Zanatta HG Bonacorso (2006) J Mol Catal A: Chem 266 100 Occurrence Handle10.1016/j.molcata.2006.10.053

    Article  Google Scholar 

  • Moreira DN, Longhi K, Frizzo CP, Zanatta N, Bonacorso HG, Martins MAP (2007) Monatsh Chem, doi: 10.1007/s00706-008-0874-8

  • H Olivier-Bourbigou L Magna (2002) J Mol Catal A: Chem 182–183 419 Occurrence Handle10.1016/S1381-1169(01)00465-4

    Article  Google Scholar 

  • P Wasserscheid T Welton (Eds) (2002) Ionic Liquids in Synthesis Wiley-VCH Verlag Stuttgart

    Google Scholar 

  • Y Xiao VM Sanjay (2005) J Organomet Chem 690 3609 Occurrence Handle10.1016/j.jorganchem.2005.04.047 Occurrence Handle1:CAS:528:DC%2BD2MXntVCktrk%3D

    Article  CAS  Google Scholar 

  • II Gerus MG Gorbunova SI Vdovenko YL Yagupolskii (1990) Zh Org Khim 26 1877 Occurrence Handle1:CAS:528:DyaK3MXktVyiu7g%3D

    CAS  Google Scholar 

  • SV Pazenok II Gerus EA Chaika YL Yagupolskii (1989) Zh Org Khim 25 379 Occurrence Handle1:CAS:528:DyaL1MXkt1Cqtrc%3D

    CAS  Google Scholar 

  • KS Mali GB Dutt T Mukherjee (2005) J Chem Phys 123 174504 Occurrence Handle10.1063/1.2102847 Occurrence Handle1:STN:280:DC%2BD2Mnos1Kqtg%3D%3D

    Article  CAS  Google Scholar 

  • Aki SNVK, Brennecke JF, Samanta A (2001) Chem Commun:413

  • C Wakai A Oleinikova M Ott HJ Weingärtner (2005) Phys Chem B 109 17028 Occurrence Handle10.1021/jp053946+ Occurrence Handle1:CAS:528:DC%2BD2MXosVGgsLw%3D

    Article  CAS  Google Scholar 

  • C Wakai A Oleinikova HJ Weingärtner (2006) J Phys Chem B 110 5824 Occurrence Handle10.1021/jp0601973 Occurrence Handle1:CAS:528:DC%2BD28Xhs12ks74%3D

    Article  CAS  Google Scholar 

  • Sheldrick GM, SHELXS-97 (1997) Program for Crystal Structure Solution, University of Göttingen, Germany

  • Sheldrick GM, SHELXL-97 (1997) Program for Crystal Structure Refinement, University of Göttingen, Germany

  • LJ Farrugia InstitutionalAuthorNameORTEP-III for Windows (1997) J Appl Crystallogr 30 565 Occurrence Handle10.1107/S0021889897003117 Occurrence Handle1:CAS:528:DyaK2sXnt1KgsLg%3D

    Article  CAS  Google Scholar 

  • R Souza PAZ Suarez CS Consorti J Dupont (2002) Org Synth 79 236

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Marcos A. P. Martins.

Additional information

Correspondence: Marcos A. P. Martins, Núcleo de Química de Heterociclos – NUQUIMHE, Universidade Federal de Santa Maria, Santa Maria, RS, Brazil.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Martins, M., Guarda, E., Frizzo, C. et al. An ionic liquid as reaction medium for the synthesis of halo-containing β-enaminones at room temperature. Monatsh Chem 139, 1321–1327 (2008). https://doi.org/10.1007/s00706-008-0923-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-008-0923-3

Keywords

Navigation