Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 9
2,151
Views
49
CrossRef citations to date
0
Altmetric
Original Articles

One-Pot Wittig and Knoevenagel Reactions in Ionic Liquid as Convenient Methods for the Synthesis of Coumarin Derivatives

&
Pages 1666-1678 | Received 11 Oct 2008, Published online: 02 Apr 2009

REFERENCES

  • Domling , A. ; Ugi , I. Multicomponent reactions with isocyanides . Angew. Chem., Int. Ed. 2000 , 39 , 3168 – 3210 .
  • Terret , N. K. ; Gardener , M. ; Gordon , D. W. ; Kobylecki , R. J. ; Steele , J. Combinatorial synthesis—The design of compound libraries and their application to drug discovery . Tetrahedron 1995 , 51 , 8135 – 8173 .
  • Anastas , P. ; Williamson , T. Green Chemistry: Frontiers in Benign Chemical Synthesis and Procedures ; Oxford Science : Oxford , 1998 .
  • Welton , T. Room-temperature ionic liquids: Solvents for synthesis and catalysis . Chem. Rev. , 1999 , 99 , 2071 , and references cited therein .
  • Suarez , P. A. Z. ; Dullius , J. E. L. ; Einloft , S. ; De Souza , R. ; Dupont , J. The use of new ionic liquids in two-phase catalytic hydrogenation reaction by rhodium complexes . Polyhedron , 1996 , 15 , 1217 .
  • Dyson , P. J. ; Ellis , D. J. ; Parker , D. G. ; Welton , T. Arene hydrogenation in a room-temperature ionic liquid using a ruthenium cluster catalyst . Chem. Commun. 1999 , 25 .
  • Carmichael , A. J. ; Earle , M. J. ; Holbrey , J. D. ; McCormac , P. B. ; Seddon , K. R. The Heck reaction in ionic liquids: A multiphasic catalyst system . Org. Lett. 1999 , 1 , 997 .
  • Naser-Hijazi , B. ; Stolze , B. ; Zanker , K. S. Second Proceedings of the International Society of Coumarin Investigators ; Springer : Berlin , 1994 .
  • Cottiglia , F. ; Loy , G. ; Garau , D. ; Floris , C. ; Casu , M. ; Pompei , R. ; Bonsignore , L. ; Antimicrobial evaluation of coumarins and flavonoids from the stems of Daphne gnidium L . Phytomedicine 2001 , 8 ( 4 ), 302 – 305 .
  • Cook , C. E. ; Corley , R. C. ; Wall , M. E. ; Flavonoids , I. Synthesis of 2,2-dialkyl-Δ3-isoflavenes from coumarins . J. Org. Chem. 1965 , 30 ( 12 ), 4114 – 4120 .
  • Trost , B. M. ; Toste , F. D. A new palladium-catalyzed addition: A mild method for the synthesis of coumarins . J. Am. Chem. Soc. 1996 , 118 ( 2 ), 6305 – 6306 .
  • Scott , J. L. ; Raston , C. L. Solvent-free synthesis of 3-carboxycoumarins . Green Chem. 2000 , 2 , 245 – 247 .
  • Ramani , A. ; Chanda , B. M. ; Velu , S. ; Sivasanker , S. One-pot synthesis of coumarins: Catalysis by the solid base, calcined Mg-Al hydrotalcite . Green Chem. 1999 , 1 , 163 – 165 .
  • Saunders , J. Top Drugs: Top Synthetic Routes ; Oxford University Press : Oxford , 2000 ; Chapter 3 .
  • Corma , A. ; Martin-Aranda , R. M. ; Sanchez , F. In: Heterogeneous Catalysis and Fine Chemicals II: Proceedings of the 2nd International Symposium : M. Poitiers , et al. (Eds.); Elsevier : Amsterdam , 1991 ; p. 503 .
  • 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 ( 6 ), 785 – 790 .
  • 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 ( 20 ), 3501 – 3503 .
  • Valizadeh , H. ; Shockravi , A. Microwave-assisted Claisen rearrangement: Application to the synthesis of angelicin derivatives. J. Heterocycl. Chem. 2006, 43, 763–765.
  • Shockravi , A. ; Shargi , H. ; Valizadeh , H. ; Heravi , M. M. Solvent-free synthesis of coumarins . Phosphorus, Sulfur Silicon Relat. Elem. 2002 , 177 , 2555 – 2559 .
  • Alvim , J. Jr. ; Dias , R. L. A. ; Castilho , M. S. ; 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 ( 4 ), 763 – 773 .
  • Corrie , J. E. T. Thiol-reactive fluorescent probes for protein labeling . J. Chem. Soc., Perkin Trans. 1 1994 , 20 , 2975 – 2982 .
  • Horning , E. C. ; Horning , M. G. Coumarins from 2-hydroxy-3-methoxybenzaldehyde . J. Am. Chem. Soc. 1947 , 69 ( 4 ), 968 – 969 .
  • Harayama , T. ; Nakatsuka , K. ; Nishioka , H. ; Murakami , K. ; Ohmori , Y. ; Takeuchi , Y. ; Ishii , H. ; Kenmotsu , K. Convenient synthesis of a simple coumarin from salicylaldehyde and Wittig reagent (III): Synthesis of nitrocoumarins . Heterocycles 1994 , 38 ( 12 ), 2729 – 2738 .
  • Villieras , J. ; Ramband , M. ; Graft , M. La reaction de Wittig–Horner en milieu heterogene VI: Selectivite de la reaction sur des composes bifonctionnels . Tetrahedron Lett. 1985 , 26 ( 1 ), 53 – 56 .
  • Gramer , F. D. ; Windel , H. Über Einschlußverbindungen, X. Mitteil.: Die blauen jodverbindungen der cumarine und anderer verwandter verbindungen . Chem. Ber. 1956 , 89 , 354 – 365 .
  • 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 , 2555 – 2559 .
  • Harayama , T. ; Nakatsuka , K. ; Nishioka , H. ; Murakami , K. ; Hayashida , N. ; Ishii , H. Convenient synthesis of a simple coumarin from salicylaldehyde and Wittig reagent (II): synthesis of bromo- and methoxycarbonylcoumarins . Chem. Pharm. Bull. 1994 , 42 ( 10 ), 2170 – 2173 .
  • Morgan , G.T. ; Mickletwait , M. G. F. 6-Aminocoumarin . J. Chem. Soc. 1904 , 85 , 1230 .
  • Palimkar , S. S. ; Siddiqui , S. A. ; Thomas , D. ; Lahoti , R. J. ; Srinivasan , K. V. Ionic liquid–promoted regiospecific Friedlander annulation: Novel synthesis of quinolines and fused polycyclic quinolines . J. Org. Chem. 2003 , 68 , 9371 – 9378 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.