Imidazolium-Based Phosphinite Ionic Liquid (IL-OPPh₂) as Reusable Catalyst and Solvent for the Knoevenagel Condensation Reaction

REFERENCES

• Kennedy , R. O. ; Tharnes , R. D. Coumarins: Biology, Application and Mode of Action ; Wiley : Chichester , 1997 .
   Google Scholar
• Murray , R. D. H. ; Medez , J. ; Brown , S. A. The Natural Coumarins: Occurrence, Chemistry, and Biochemistry ; Wiley : New York , 1982 .
   Google Scholar
• Schönberg , A. ; Latif , N. Furochromones and coumarins, XI: The molluscicidal activity of bergapten, isopimpinillin, and xanthotoxin . J. Am. Chem. Soc. 1954 , 76 , 6208 .
   Web of Science ®Google Scholar
• Li , T.-S. ; Zhang , Z.-H. ; Yang , F. ; Fu , C.-G. Montmorillonite clay catalysis, part 7: An environmentally friendly procedure for the synthesis of coumarins via Pechmann condensation of phenols with ethyl acetoacetate . J. Chem. Res., Synop. 1998 , 1 , 38 – 39 .
   Web of Science ®Google Scholar
• Gunnewegh , E. A. ; Hoefnagel , A. J. ; Bekkum , H. V. Zeolite catalysed synthesis of coumarin derivatives . J. Mol. Catal. A: Chem. 1995 , 100 , 87 – 92 .
   Web of Science ®Google Scholar
• Frére , S. ; Thiéry , V. ; Besson , T. Microwave acceleration of the Pechmann reaction on graphite/montmorillonite K10: Application to the preparation of 4-substituted 7-aminocoumarins . Tetrahedron Lett. 2001 , 42 , 2791 – 2794 .
   Web of Science ®Google Scholar
• Hoefnagel , A. J. ; Geenewagh , E. A. ; Downing , R. S. ; Bekkum , H. V. Synthesis of 7-hydroxycoumarins catalyzed by solid acid catalysts . J. Chem. Soc., Chem. Commun. 1995 , 225 – 226 .
   Google Scholar
• Singh , P. R. ; Singh , D. U. ; Samant , S. D. Sulphamic acid—An efficient and cost-effective solid acid catalyst for the Pechmann reaction . Synlett 2004 , 11 , 1909 – 1912 .
   Google Scholar
• Valizadeh , H. ; Shockravi , A. An efficient procedure for the synthesis of coumarin derivatives using TiCl4 as catalyst under solvent-free conditions . Tetrahedron Lett. 2005 , 46 , 3501 – 3503 .
   Web of Science ®Google Scholar
• Richardhein , W. ; Melvin , J. Ion-exchange resin catalysis of the Knoevenagel condensation of ketones . J. Org. Chem. 1961 , 26 , 4874 – 4878 .
   Google Scholar
• Rand , L. ; Haidukewych , D. ; Dolinski , R. J. Reactions catalyzed by potassium fluoride, V: The kinetics of the Knoevenagel reaction . J. Org. Chem. 1966 , 31 , 1272 – 1274 .
   Google Scholar
• Ernst , S. ; Hartmann , M. ; Sauerbeck , S. ; Bongers , T. A novel family of solid basic catalysts obtained by nitridation of crystalline microporous aluminosilicates and aluminophosphates . Appl. Catal. A: Gen. 2000 , 200 , 117 – 123 .
   Web of Science ®Google Scholar
• Choudary , B. M. ; Kantam , M. L. ; Sreekanth , P. ; Bandopadhyay , T. ; Figueras , F. ; Tuel , A. Knoevenagel and aldol condensations catalysed by a new diamino-functionalised mesoporous material . J. Mol. Catal. A: Chem. 1999 , 142 , 361 – 365 .
   Google Scholar
• Subba , Y. ; Rao , V. ; Choudary , B. M. Knoevenagel condensation catalysed by new montmorillonitesilylpropylethylenediamine . Synth. Commun. 1991 , 21 , 1163 – 1166 .
   Google Scholar
• Kubota , Y. ; Nishizaki , Y. ; Sugi , Y. High catalytic activity of as-synthesized, ordered porous silicate–quaternary ammonium composite for Knoevenagel condensation . Chem. Lett. 2000 , 29 , 998 – 999 .
   Web of Science ®Google Scholar
• Aramendia , M. A. ; Borau , V. ; Jimenez , C. ; Marinas , J. M. ; Romero , F. J. Activity of alkaline and alkaline-earth carbonates as heterogeneous catalysts for the Knoevenagel condensation between benzaldehyde and malononitrile . Chem. Lett. 1995 , 24 , 279 – 280 .
   Google Scholar
• Valizadeh , H. ; Mamaghani , M. ; Badrian , A. Effect of microwave irradiation on reaction of arylaldehyde derivatives with some active methylene compounds in aqueous media . Synth. Commun. 2005 , 35 , 785 – 790 .
   Web of Science ®Google Scholar
• Valizadeh , H. ; Vaghefi , H. One-pot Wittig and Knoevenagel reactions in ionic liquid as convenient methods for the synthesis of coumarin derivatives . Synth. Commun. 2009 , 39 , 1666 – 1678 .
   Web of Science ®Google Scholar
• Welton , T. Room-temperature ionic liquids: Solvents for synthesis and catalysis . Chem. Rev. 1999 , 99 , 2071 – 2084 , and references cited therein.
   PubMed Web of Science ®Google Scholar
• Gruttadauria , M. ; Riela , S. ; Lo Meo , P. ; D'Anna , F. ; Noto , R. Supported ionic liquid asymmetric catalysis: A new method for chiral catalyst recycling: The case of proline-catalyzed aldol reaction. Tetrahedron Lett. 2004, 45, 6113–6116.
   Web of Science ®Google Scholar
• Yue , C. ; Mao , A. ; Wei , Y. ; Lu , M. Knoevenagel condensation reaction catalyzed by task-specific ionic liquid under solvent-free conditions . Catal. Commun. 2008 , 9 , 1571 – 1574 .
   Web of Science ®Google Scholar
• Paun , C. ; Barklie , J. ; Goodrich , P. ; Gunaratne , H. Q. N. ; McKeown , A. ; Pârvulescu , V. I. ; Hardacre , C. Supported and liquid-phase task-specific ionic liquids for base-catalysed Knoevenagel reactions . J. Mol. Catal. A: Chem. 2007 , 269 , 64 – 71 .
   Web of Science ®Google Scholar
• Davey , P. N. ; Forsyth , S. ; Gunaratne , H. ; Hardacre , C. ; McKeown , A. ; McMath , S. E. J. ; Rooney , D. W. ; Seddon , K. R. Synthesis of 3-(4-tert-butylphenyl)-2-propen-1-one, a precursor to Lilial, via an aldol condensation in an ionic liquid . Green Chem. 2005 , 7 , 224 – 229 .
   Google Scholar
• Holbrey , J. D. ; Turner , M. B. ; Reichert , W. M. ; Rogers , R. D. New ionic liquids containing appended hydroxyl functionality from the atom-efficient, one-pot reaction of 1-methylimidazole and acid with propylene oxide . Green Chem. 2003 , 5 , 731 – 736 .
   Web of Science ®Google Scholar
• Iranpoor , N. ; Firouzabadi , H. ; Azadi , R. A new diphenylphosphinite ionic liquid (IL-OPPh2) as reagent and solvent for highly selective bromination, thiocyanation, or isothiocyanation of alcohols and trimethylsilyl and tetrahydropyranyl ethers . Tetrahedron Lett. 2006 , 47 , 5531 – 5534 .
   Web of Science ®Google Scholar
• Zhang , M. ; Zhang , A.Q. ; Tang , X. H. Knoevenagel condensation catalyzed by chitosan . Chin. J. Org. Chem. 2004 , 24 , 1106 – 1107 ; Chem. Abstr. 2005 , 142 , 240170 .
   Web of Science ®Google Scholar
• Jin , T.-S. ; Guo , J.-J. ; Liu , H.-M. ; Liu , T.-S. Synthesis of ethyl α-cyanocinnamates catalyzed by Al2O3-OK solid base . Synth. Commun. 2003 , 33 , 783 – 788 .
   Web of Science ®Google Scholar
• Jitendra , R. H. ; Susheel , J. N. ; Manikrao , M. S. Lewis acidic ionic liquids for the synthesis of electrophilic alkenes via the Knoevenagel condensation . Tetrahedron Lett. 2002 , 43 , 1127 – 1130 .
   Google Scholar
• Shockravi , A. ; Shargi , H. ; Valizadeh , H. ; Heravi , M. M. Solvent-free synthesis of coumarins . Phosphorus, Sulfur Silicon Relat. Elem. 2002 , 177 , 2555 – 2559 .
   Web of Science ®Google Scholar
• Alvim , J. Jr. ; Dias Ricardo , L. A. ; Marcelo , S. C. ; Glaucius , O. ; Corrêa , A. G. Preparation and evaluation of a coumarin library towards the inhibitory activity of the enzyme gGAPDH from Trypanosoma cruzi . J. Braz. Chem. Soc. 2005 , 16 , 763 – 773 .
   Web of Science ®Google Scholar
• Corrie , J. E. T. Thiol-reactive fluorescent probes for protein labeling . J. Chem. Soc., Perkin Trans. 1 1994 , 20 , 2975 – 2982 .
   Google Scholar
• Horning , E. C. ; Horning , M. G. Coumarins from 2-hydroxy-3-methoxybenzaldehyde . J. Am. Chem. Soc. 1947 , 69 , 968 – 969 .
   PubMedGoogle Scholar
• Bogdal , D. Coumarins—Fast synthesis by the Knoevenagel condensation under microwave irradiation. Available at http://www.ch.ic.ac.uk/ectoc/echet98/pub/087/index.html
   Google Scholar