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.
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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
A Laurent J Diab IL Dréan (1997) J Fluorine Chem 84 145 Occurrence Handle10.1016/S0022-1139(97)00056-0
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
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
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
Lyle FR (1985) US Patent 5 973 257
FR Lyle (1985) Chem Abstr 65 2870
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
J Lin L-F Zhang (2007) Monatsh Chem 138 77 Occurrence Handle10.1007/s00706-006-0565-2 Occurrence Handle1:CAS:528:DC%2BD2sXksl2k
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
Z-H Zhang J-Y Hu (2006) J Braz Chem Soc 17 1447 Occurrence Handle1:CAS:528:DC%2BD28XhtlWksLnN
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
J-T Liu X-J Yang F-L Zhao (2004) J Fluorine Chem 125 415 Occurrence Handle10.1016/j.jfluchem.2004.03.006
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
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
N Zanatta DC Flores SS Amaral HG Bonacorso MAP Martins AFC Flores (2005) Synlett 20 3079 Occurrence Handle10.1055/s-2005-922747
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
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
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
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
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
P Wasserscheid T Welton (Eds) (2002) Ionic Liquids in Synthesis Wiley-VCH Verlag Stuttgart
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
II Gerus MG Gorbunova SI Vdovenko YL Yagupolskii (1990) Zh Org Khim 26 1877 Occurrence Handle1:CAS:528:DyaK3MXktVyiu7g%3D
SV Pazenok II Gerus EA Chaika YL Yagupolskii (1989) Zh Org Khim 25 379 Occurrence Handle1:CAS:528:DyaL1MXkt1Cqtrc%3D
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
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
C Wakai A Oleinikova HJ Weingärtner (2006) J Phys Chem B 110 5824 Occurrence Handle10.1021/jp0601973 Occurrence Handle1:CAS:528:DC%2BD28Xhs12ks74%3D
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
R Souza PAZ Suarez CS Consorti J Dupont (2002) Org Synth 79 236
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Correspondence: Marcos A. P. Martins, Núcleo de Química de Heterociclos – NUQUIMHE, Universidade Federal de Santa Maria, Santa Maria, RS, Brazil.
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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
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DOI: https://doi.org/10.1007/s00706-008-0923-3