One-Pot wittig and knoevenagel reactions in ionic liquid as convenient methods for the synthesis of coumarin derivatives

Synthetic Communications

Volumn 39, Issue 9, 2009, Pages 1666-1678

  Valizadeh, Hassan ^a   Vaghefi, Sevil ^a  

^a AZARBAIJAN SHAHID MADANI UNIVERSITY   (Iran)

Author keywords

Coumarins; Ionic liquid; Knoevenagel reaction; Wittig reaction

Indexed keywords

2 HYDROXYBENZALDEHYDE DERIVATIVE; 2 OXO 2H CHROMENE; 6 BROMO 2 OXO 2H CHROMENE; 6 NITRO 2 OXO 2H CHROMENE; 7 BROMO 2 OXO 2H CHROMENE; 7 HYDROXY 2 OXO 2H CHROMENE; 7 METHOXY 2 OXO 2H CHROMENE; 8 BROMO 2 OXO 2H CHROMENE; 8 NITRO 2 OXO 2H CHROMENE; COUMARIN DERIVATIVE; DIETHYLCHLOROMALONATE DERIVATIVE; DIETHYLMALONATE; DIMETHYLCHLOROMALONATE DERIVATIVE; DIMETHYLMALONATE; ETHYL 2 OXO 2H CHROMENE 3 CARBOXYLATE; ETHYL 7 DIETHYLAMINO 2 OXO 2H CHROMENE 3 CARBOXYLATE; ETHYL 7 HYDROXY 2 OXO 2H CHROMENE 3 CARBOXYLATE; ETHYL 7 METHOXY 2 OXO 2H CHROMENE 3 CARBOXYLATE; ETHYL 7,8 DIHYDROXY 2 OXO 2H CHROMENE 3 CARBOXYLATE; ETHYL 8 BROMO 7 HYDROXY 2 OXO 2H CHROMENE 3 CARBOXYLATE; ETHYL 8 BROMO 7 METHOXY 2 OXO 2H CHROMENE 3 CARBOXYLATE; ETHYL 8 HYDROXY 2 OXO 2H CHROMENE 3 CARBOXYLATE; ETHYL 8 METHOXY OXO 2H CHROMENE 3 CARBOXYLATE; ETHYLCHLOROACETATE DERIVATIVE; IONIC LIQUID; MALONIC ACID; METHYL 7 HYDROXY 2 OXO 2H CHROMENE 3 CARBOXYLATE; METHYL 7 METHOXY 2 OXO 2H CHROMENE 3 CARBOXYLATE; METHYLCHLOROACETATE DERIVATIVE; SALICYLALDEHYDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; KNOEVENAGEL CONDENSATION; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; WITTIG REACTION;

EID: 67650072422     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802573163     Document Type: Article

References (29)

1. Domling, A.; Ugi, I. Multicomponent reactions with isocyanides. Angew. Chem., Int. Ed. 2000, 39, 3168-3210.
2. 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.
3. Anastas, P.; Williamson, T. Green Chemistry: Frontiers in Benign Chemical Synthesis and Procedures; Oxford Science: Oxford, 1998.
4. Welton, T. Room-temperature ionic liquids: Solvents for synthesis and catalysis. Chem. Rev., 1999, 99, 2071, and references cited therein.
5. 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.
6. 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.
7. 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.
8. Naser-Hijazi, B.; Stolze, B.; Zanker, K. S. Second Proceedings of the International Society of Coumarin Investigators; Springer: Berlin, 1994.
9. 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.
10. 3-isoflavenes from coumarins. J. Org. Chem. 1965, 30 (12), 4114-4120.
11. 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.
12. Scott, J. L.; Raston, C. L. Solvent-free synthesis of 3-carboxycoumarins. Green Chem. 2000, 2, 245-247.
13. 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.
14. Saunders, J. Top Drugs: Top Synthetic Routes; Oxford University Press: Oxford, 2000; Chapter 3.
15. Corma, A.; Martin-Aranda, R. M.; Sanchez, F. In: Heterogeneous Catalysis and Fine Chemicals II: Proceedings ofthe 2nd International Symposium:M. Poitiers, Guisnet, et al. (Eds.); Elsevier: Amsterdam, 1991; p. 503.
16. 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.
17. 4 as catalyst under solvent-free conditions. Tetrahedron Lett. 2005, 46 (20), 3501-3503.
18. Valizadeh, H.; Shockravi, A. Microwave-assisted Claisen rearrangement: Application to the synthesis of angelicin derivatives. J. Heterocycl. Chem. 2006, 43, 763-765.
19. Shockravi, A.; Shargi, H.; Valizadeh, H.; Heravi, M. M. Solvent-free synthesis of coumarins. Phosphorus, Sulfur Silicon Relat. Elem. 2002, 177, 2555-2559.
20. 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.
21. Corrie, J. E. T. Thiol-reactive fluorescent probes for protein labeling. J. Chem. Soc., Perkin Trans. 1 1994, 20, 2975-2982.
22. Horning, E. C.; Horning, M. G. Coumarins from 2-hydroxy-3-methoxyben- zaldehyde. J. Am. Chem. Soc. 1947, 69 (4), 968-969.
23. 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 nitrocou- marins. Heterocycles 1994, 38 (12), 2729-2738.
24. 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.
25. Gramer, F. D.; Windel, H. Über Einschlußverbindungen, X. Mitteil.: Die blauen jodverbindungen der cumarine und anderer verwandter verbindungen. Chem. Ber. 1956, 89, 354-365.
26. 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.
27. 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.
28. Morgan, G.T.; Mickletwait, M. G. F. 6-Aminocoumarin. J. Chem. Soc. 1904, 85, 1230.
29. 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.