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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 42, 2012 - Issue 23
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Original Articles

Novel Task-Specific Ionic Liquids as Solvents for Michael Addition of Methylene Active Compounds to Chalcones Without Any Catalyst

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Pages 3455-3462 | Received 18 Feb 2011, Published online: 02 Aug 2012

REFERENCES

  • Ye , W. P. ; Xu , J. Y. ; Tan , C. T. ; Tan , C. H. 1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD)–catalyzed Michael reactions . Tetrahedron Lett. 2005 , 46 , 6875 – 6878 .
  • Kubota , Y. ; Ikeya , H. ; Sugi , Y. ; Yamada , T. ; Tatsumi , T. Organic–inorganic hybrid catalysts based on ordered porous structures for Michael reaction . J. Mol. Catal. A: Chem. 2006 , 249 , 181 – 190 .
  • Mori , K. ; Oshiba , M. ; Hara , T. ; Mizugaki , T. ; Ebitani , K. ; Kaneda , K. Creation of monomeric La complexes on apatite surfaces and their application as heterogeneous catalysts for Michael reactions . New J. Chem. 2006 , 30 , 44 – 52 .
  • Zahouily , M. ; Bahlaodhuan , B. ; Aadil , M. ; Ray , A. ; Sebti , S. Natural phosphate doped with potassium fluoride: Efficient catalyst for the construction of a carbon–carbon bond . Org. Pro. Res. Develop. 2004 , 8 , 275 – 278 .
  • Ma , Y. M. ; Zhang , Y. M. Michael additions of active methylene compounds to chalcones promoted by samarium(III) iodide . Synth. Commun. 2002 , 32 , 819 – 823 .
  • Meciarova , M. ; Toma , S. Michael additions of methylene active compounds to chalcone in ionic liquids without any catalyst: The peculiar properties of ionic liquids. Chem. Eur. J. 2007, 13, 1268–1272.
  • Rao , H. S. P. ; Jothilingam , S. Solvent-free microwave-mediated Michael addition reactions . J. Chem. Sci. 2005 , 117 , 323 – 328 .
  • Li , J. T. ; Cui , Y. ; Chen , G. F. ; Cheng , Z. L. ; Li , T. S. Michael addition catalyzed by potassium hydroxide under ultrasound . Synth. Commun. 2003 , 33 , 353 – 359 .
  • (a) Miao , W. W. ; Chan , T. H. Ionic-liquid-supported synthesis: A novel liquid-phase strategy for organic synthesis . Acc. Chem. Res. 2006 , 39 , 897 – 908 ; (b) Ying , A. G. ; Chen , X. Z. ; Ye , W. ; Zhang , D. F. ; Liu , L. ; Chen , J. H. Application of ionic liquids in organic synthesis promoted by microwave irradiation . Prog. Chem. 2008 , 20 , 1642 – 1650 ; (c) Ying , A. G. ; Ye , W. D. ; Liu , L. ; Wu , G. F. ; Chen , X. Z. ; Qian , S. ; Zhang , Q. P. Progress in the application of ionic liquids to organic synthesis . Chin. J. Org. Chem. 2008 , 28 , 2081 – 2094 .
  • (a) Ranu , B. C. ; Banerjee , S. Solvent-controlled highly selective bis- and monoallylation of active methylene compounds by allyl acetate with palladium (0) nanoparticle . Org. Lett. 2005 , 7 , 3049 – 3052 ; (b) Ranu , B. C. ; Banerjee , S. ; Jana , R. Ionic liquid as catalyst and solvent: The remarkable effect of a basic ionic liquid, [bmIm]OH, on Michael addition and alkylation of active methylene compounds . Tetrahedron 2007 , 63 , 776 – 782 .
  • (a) Ying , A. G. ; Liu , L. ; Wu , G. F. ; Chen , G. ; Chen , X. Z. ; Ye , W. D. Aza-Michael addition of aliphatic or aromatic amines to α,β-unsaturated compounds catalyzed by a DBU-derived ionic liquid under solvent-free conditions . Tetrahedron Lett. 2009 , 50 , 1653 – 1657 ; (b) Ying , A. G. ; Wang , L. M. ; Deng , H. X. ; Chen , J. H. ; Chen , X. Z. ; Ye , W. D. Green and efficient hetero-Michael additions of aromatic amines to α,β-unsaturated ketones catalyzed by DBU-based task-specific ionic liquids without solvent . Arkivoc 2009 , 11 , 288 – 298 .
  • (a) Ying , A. G. ; Liu , L. ; Wu , G. F. ; Chen , X. Z. ; Ye , W. D. ; Chen , J. H. ; Zhang , K. Y. Knoevenagel condensation catalyzed by DBU Brønsted ionic liquid without solvent . Chem. Res. Chin. Univ. 2009 , 25 , 876 – 881 ; (b) Ying , A. G. ; Wang , L. M. ; Wang , L. L. ; Chen , X. Z. ; Ye , W. D. Green and efficient Knoevenagel condensation catalyzed by a DBU-based ionic liquid in water . J. Chem. Res. 2010 , 30 – 33 .
  • Li , J. T. ; Chen , G. F. ; Xu , W. Z. ; Li , T. S. The Michael reaction catalyzed by KF/basic alumina under ultrasound irradiation . Ultrason. Sonochem. 2003 , 10 , 115 – 118 .
  • Liang , D. P. ; Xin , X. ; Gao , H. ; Duan , H. F. ; Lin , Y. J. Chem. Res. Chin. Univ. 2009 , 25 , 169 – 173 .
  • Raghukumar , V. ; Murugan , P. ; Ramakrishnan , V. T. A facile one-pot synthesis of m-terphenyl and biaryl derivatives . Synth. Commun. 2001 , 31 , 3497 – 3505 .

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