Task-Specific Ionic Liquid as Reagent and Reaction Medium for the One-Pot Horner–Wadsworth–Emmons–Type Reaction Under Microwave Irradiation

REFERENCES

• Kennedy , R. O. ; Tharnes , R. D. Coumarins: Biology, Application, and Mode of Action ; Wiley and Sons : Chichester , 1997 .
   Google Scholar
• Kashman , Y. ; Gustafson , K. R. ; Fuller , R. ; Cardellina , J. H. ; McMahon , J. B. ; Currens , M. J. ; Buckheit , R. W. ; Hughes , S. H. ; Cragg , G. M. ; Boyd , M. R. HIV inhibitory natural products, part 7: The calanolides, a novel HIV-inhibitory class of coumarin derivatives from the tropical rainforest tree, Calophyllum lanigerum . J. Med. Chem. 1992 , 35 , 2735 – 2743 .
   PubMed Web of Science ®Google Scholar
• Cravotto , G. ; Nano , G. M. ; Palmisano , G. ; Tagliapietra , S. An asymmetric approach to coumarin anticoagulants via hetero-Diels–Alder cycloaddition . Tetrahedron: Asymmetry 2001 , 12 , 707 .
   Web of Science ®Google Scholar
• Zabradnik , M. The Production and Application of Fluorescent Brightening Agents ; John Wiley and Sons : New York , 1992 .
   Google Scholar
• Maeda , M. Laser Dyes ; Academic : New York , 1994 .
   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
• Donnelly , B. J. ; Donnelly , D. M. X. ; Sullivan , A. M. O. Dalbergia species—VI: The occurrence of melannein in the genus Dalbergia . Tetrahedron 1968 , 24 , 2617 – 2622 .
   Web of Science ®Google Scholar
• Bigi , F. ; Chesini , L. ; Maggi , R. ; Sartori , G. Montmorillonite KSF as an inorganic, water stable, and reusable catalyst for the Knoevenagel synthesis of coumarin-3-carboxylic acids . J. Org. Chem. 1999 , 64 , 1033 – 1035 .
   PubMed Web of Science ®Google Scholar
• Shirner , R. L. The Reformatsky reaction . Org. React. 1942 , 1 , 1 .
   Google Scholar
• Yavari , I. ; Hekmat-shoar , R. ; Zonuzi , A. A new and efficient route to 4-carboxymethylcoumarins mediated by vinyltriphenylphosphonium salt . Tetrahedron Lett. 1998 , 39 , 2391 – 2392 .
   Web of Science ®Google Scholar
• Shockravi , A. ; Valizadeh , H. ; Heravi , M. M. A one-pot and convenient synthesis of coumarins in solventless system . Phosphorus, Sulfur Silicon Relat. Elem. 2003 , 178 , 501 – 504 .
   Web of Science ®Google Scholar
• Wilkes , J. S. A short history of ionic liquids—From molten salts to neoteric solvents . Green Chem. 2002 , 4 , 73 .
   Web of Science ®Google Scholar
• Wasserscheid , P. ; Welton , T. Ionic Liquids in Synthesis ; Wiley-VCH : Weinheim , Germany , 2003 .
   Google Scholar
• Hagiwara , H. ; Sugawara , Y. ; Isobe , K. ; Hoshi , T. ; Suzuki , T. Immobilization of Pd(OAc)2 in ionic liquid on silica: Application to sustainable Mizoroki-Heck reaction . Org. Lett. 2004 , 6 , 2325 – 2328 .
   PubMed Web of Science ®Google Scholar
• Gmouh , S. ; Yang , H. ; Vaultier , M. Activation of bismuth(III) derivatives in ionic liquids: Novel and recyclable catalytic systems for Friedel−Crafts acylation of aromatic compounds . Org. Lett. 2003 , 5 , 2219 – 2222 .
   PubMed Web of Science ®Google Scholar
• Kabalka , G. W. ; Dong , G. ; Venkataiah , B. Rhodium-catalyzed cross-coupling of allyl alcohols with aryl- and vinylboronic acids in ionic liquids . Org. Lett. 2003 , 5 , 893 – 895 .
   Google Scholar
• Boxwell , C. V. ; Dyson , P. J. ; Ellis , D. J. ; Welton , T. A highly selective arene hydrogenation catalyst that operates in ionic liquid . J. Am. Chem. Soc. 2002 , 124 , 9334 – 9335 .
   PubMed Web of Science ®Google Scholar
• Dabiri , M. ; Salehi , P. ; Baghbanzadeh , M. ; Shakouri , M. ; Otokesh , S. ; Ekrami , T. ; Doosti , R. Efficient and eco-friendly synthesis of dihydropyrimidinones, bis(indolyl)methanes, and N -alkyl and N -arylimides in ionic liquids . J. Iran. Chem. Soc. 2007 , 4 , 393 – 401 .
   Web of Science ®Google Scholar
• Sharifi , A. ; Abaee , M. S. ; Mirzaei , M. ; Salimi , R. Ionic liquid–mediated Darzens condensation: An environmentally friendly procedure for the room-temperature synthesis of α,β-epoxy ketones . J. Iran. Chem. Soc. 2008 , 5 , 135 – 139 .
   Google Scholar
• Tajik , H. ; Niknam , K. ; Parsa , F. Using acidic ionic liquid 1-butyl-3-methylimidazolium hydrogen sulfate in selective nitration of phenols under mild conditions . J. Iran. Chem. Soc. 2009 , 6 , 159 – 164 .
   Web of Science ®Google Scholar
• Dupont , J. ; de Souza , R. F. ; Suarez , P. A. Z. Ionic liquid (molten salt) phase organometallic catalysis . Chem. Rev. 2002 , 102 , 3667 – 3692 .
   PubMed Web of Science ®Google Scholar
• Qiao , K. ; Yakoyama , C. Novel acidic ionic liquids catalytic systems for Friedel–Crafts alkylation of aromatic compounds with alkenes. Chem. Lett. 2004, 33, 472.
   Web of Science ®Google Scholar
• Sun , W. ; Xia , C.-G. ; Wang , H.-W. Synthesis of aziridines from imines and ethyl diazoacetate in room temperature ionic liquids . Tetrahedron Lett. 2003 , 44 , 2409 – 2411 .
   Web of Science ®Google Scholar
• Kamal , A. ; Chouhan , G. A task-specific ionic liquid [bmim]SCN for the conversion of alkyl halides to alkyl thiocyanates at room temperature . Tetrahedron Lett. 2005 , 46 , 1489 – 1491 .
   Web of Science ®Google Scholar
• Earle , M. J. ; Ktdare , S. P. ; Seddon , K. R. Paradigm confirmed: The first use of ionic liquids to dramatically influence the outcome of chemical reactions . Org. Lett. 2004 , 6 , 707 – 710 .
   PubMed Web of Science ®Google Scholar
• Baudequin , C. ; Boudoux , J. ; Levllain , J. ; Cahard , D. ; Gaumont , A.-C. ; Plaquevent , J.-C. Ionic liquids and chirality: Opportunities and challenges . Tetrahedron: Asymmetry 2003 , 14 , 3081 – 3093 .
   Web of Science ®Google Scholar
• Loh , T. P. ; Feng , L.-C. ; Yang , H.-Y. ; Yang , J.-Y. 1-Proline in an ionic liquid as an efficient and reusable catalyst for direct asymmetric aldol reactions . Tetrahedron Lett. 2002 , 43 , 8741 – 8743 .
   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 catalysts recycling. The case of proline-catalyzed aldol reaction . Tetrahedron Lett. 2004 , 45 , 6113 – 6116 .
   Web of Science ®Google Scholar
• Iranpoor , N. ; Firouzabadi , H. ; Azadi , R. Imidazolium-based phosphinite ionic liquid (IL-OPPh2) as Pd ligand and solvent for selective dehalogenation or homocoupling of aryl halides . J. Organomet. Chem. 2008 , 693 , 2469 – 2472 .
   Web of Science ®Google Scholar
• March , J. Advanced Organic Chemistry, Reactions, Mechanisms, and Structure ; Wiley : New York , 1992 .
   Google Scholar
• Spinella , A. ; Fortunati , T. ; Soriente , A. Microwave accelerated Wittig reactions of stabilized phosphorus ylides with ketones under solvent-free conditions . Synlett 1997 , 93 – 94 .
   Web of Science ®Google Scholar
• Matikainen , J. K. ; Kaltia , S. ; Hase , T. Wittig reactions under daylight lamp irradiation: Maximizing the yields of (E)-alkenes . Synlett 1994 , 817 – 818 .
   Google Scholar
• Patil , V. J. ; Mavers , U. Wittig reactions in the presence of silica gel . Tetrahedron Lett. 1996 , 37 , 1281 – 1284 .
   Web of Science ®Google Scholar
• Hooper , D. L. ; Garagan , S. ; Kayser , M. M. Lithium cation-catalyzed Wittig reactions . J. Org. Chem. 1994 , 59 , 1126 – 1128 .
   Web of Science ®Google Scholar
• Valizadeh , H. ; Vaghefi , S. 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
• Holbrey , J. D. ; Turner , M. B. ; Reichert , W. M. ; Rogers , R. D. New ionic liquids containing an 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