Microwave-assisted and efficient solvent-free Knoevenagel condensation. A sustainable protocol using porous calcium hydroxyapatite as catalyst

Molecules

Volumn 15, Issue 2, 2010, Pages 813-823

  Mallouk, Siham ^a   Bougrin, Khalid ^a   Laghzizil, Abdelaziz ^a   Benhida, Rachid ^b  

^a FACULTÉ DES SCIENCES   (Morocco)

^b UNIVERSITÉ DE NICE SOPHIA ANTIPOLIS   (France)

Author keywords

Catalysis; Knoevenagel; Microwave; Solvent free; Sustainable procedure

Indexed keywords

EID: 77649202539     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules15020813     Document Type: Article

References (46)

1. Tietze, L.F.; Beifuss, U. The Knoevenagel reaction. In Comprehensive Organic Synthesis; Trost, B.M., Ed.; Pergamon Press: Oxford, UK, 1991; Volume 2, pp. 341-394.
2. Jones, G. The Knoevenagel condensation. Org. React. 1967, 15, 204-599.
3. Kubota, Y.; Nishizaki, Y.; Sugi, Y. High catalytic activity of as-synthesized, ordered porous silicate quaternary qmmonium composite for Knoevenagel condensation. Chem. Lett. 2000, 29, 998-999.
4. Balalaie, S.; Sheikh-Ahmadi, M.; Bararjanian, M. Tetra-methyl ammonium hydroxide: An efficient and versatile catalyst for the one-pot synthesis of tetrahydrobenzo[b]pyran derivatives in aqueous media. Catal. Commun. 2007, 8, 1724-1728.
5. Rao, P.S.; Venkataratnam, R.V. Zinc chloride as a new catalyst for Knoevenagel condensation. Tetrahedron Lett. 1991, 32, 5821-5822.
6. Prajapati, D.; Sandhu, J.S. Cadmium iodide as a new catalyst for Knoevenagel condensation. J. Chem. Soc. Perkin Trans 1. 1993, 1, 739-740.
7. 4/THF/pyridin(I). alkyliden- und arylidenmalonester bei 0-25 e°C. Tetrahedron Lett. 1970, 54, 4723-4724.
8. Texier-Boullet, F.; Foucaud, A. Knoevenagel condensation catalysed by aluminium oxide. Tetrahedron Lett. 1982, 23, 4927-4928.
9. 2 supported heterogeneous catalysts: An environmentally benign approach. Catal. Commun. 2009, 10, 365-369.
10. Moison, H.; Texier-Boullet, F.; Foucaud, A. Knoevenagel, wittig and wittig-horner reactions in the presence of magnesium oxide or zinc oxide. Tetrahedron 1987, 43, 537-542.
11. Cabello, J.A.; Campelo, J.M.; Garcia, A.; Luna, D.; Marinas, J.M. Knoevenagel condensation in the heterogeneous phase using aluminum phosphate-aluminum oxide as a new catalyst. J. Org. Chem. 1984, 49, 5195-5197.
12. Dai, G.; Shi, D.; Zhou, L.; Huaxue, Y. Knoevenagel condensation catalyzed by potassium fluoride/alumina. Chin. J. Appl. Chem. 1995, 12, 104-108.
13. Sebti, S.; Smahi, A.; Solhy, A. Natural phosphate doped with potassium fluoride and modified with sodium nitrate: Efficient catalysts for the Knoevenagel condensation. Tetrahedron Lett. 2002, 43, 1813-1815.
14. 7, a new catalyst for Knoevenagel reaction. Catal. Commun. 2001, 2, 101-104.
15. 7. Synthesis of (E)-methyl-α-cyanocinnamates in high yields. J. Chem. Cryst. 2003, 33, 757-760.
16. Reddy, T.I.; Varma, R.S. Rare-earth (RE) exchanged NaY zeolite promoted Knoevenagel condensation. Tetrahedron Lett. 1997, 38, 1721-1724.
17. Abdallah-El Ayoubi, S.; Texier-Boullet, F. Clay-mediated synthesis of gem bis-(alkoxycarbonyl) alkenes under microwave irradiation. J. Chem. Res. (S) 1995, 205-206.
18. Angeletti, E.; Canepa, C.; Martinetti, G.; Venturello, P. Amino groups in Knoevenagel condensation. J. Chem. Soc., Perkin Trans. 1989, 1, 105-107.
19. Simpson, J.; Rathbone, D.L.; Billington, D.C. New solid phase Knoevenagel catalyst. Tetrahedron Lett. 1999, 40, 7031-7033.
20. Taha, N.; Sasson, Y.; Chidambaram, M. Phase transfer methodology for the synthesis of substituted stilbenes under Knoevenagel condensation condition. Appl. Catal. A: Gen. 2008, 350, 217-224.
21. Kumbhare, R.M.; Sridhar, M. Magnesium fluoride catalyzed Knoevenagel reaction: An efficient synthesis of electrophilic alkenes. Catal. Commun. 2008, 9, 403-405.
22. Khan, F.A.; Dash, F.J.; Satapathy, R.; Upadhyay, S.K. Hydrotalcite catalysis in ionic liquid medium: A recyclable reaction system for heterogeneous Knoevenagel and nitroaldol condensation. Tetrahedron Lett. 2004, 45, 3055-3058
23. Choudary, B.M.; Kantam, M.L.; Neeraja, V.; Rao, K.K. Layered double hydroxide fluoride: A novel solid base catalyst for C-C bond formation. Green Chem. 2001, 3, 257-260.
24. Ernst, S.; Bongers, T.; Casel, C.; Munsch, S. Cesium-modified mesoporous molecular sieves as basic catalysts for Knoevenagel condensations. Stud. Surf. Sci. Catal. 1999, 125, 367-374.
25. Rao, Y.V.S.; De Vos, D.E.; Jacobs, P.A. 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.
26. De la Cruz, P.; Diez-Barra, E.; Loupy, A.; Langa, F. Silica gel catalysed Knoevenagel condensation in dry media under microwave irradiation. Tetrahedron Lett. 1996, 37, 1113-1116.
27. Yadav, J.S.; Reddy, B.S.V.; Basak, A.K.; Visali, B.; Narsaiah, A.V.; Nagaiah, K. Phosphanecatalyzed Knoevenagel condensation: A facile synthesis of cyanoacrylates and cyanoacrylonitriles. Eur. J. Org. Chem. 2004, 2004, 546-551.
28. 3 under ultrasound irradiation. Ultrason. Sonochem. 2002, 9, 159-163.
29. Li, J.T.; Xing, C.Y.; Li, T.S. An efficient and environmentally friendly method for synthesis of arylmethylenemalononitrile catalyzed by Montmorillonite K10-ZnCl2 under ultrasound irradiation. J. Chem. Technol. Biotechnol. 2004, 79, 1275-1278.
30. Peng, Y.Q.; Song, G.H. Combined microwave and ultrasound accelerated Knoevenagel-Doebner reaction in aqueous media: A green route to 3-aryl acrylic acids. Green Chem. 2003, 6, 704-706.
31. Feroci, M.; Orsini, M.; Palombi, L.; Inesi, A. Electrochemically induced Knoevenagel condensation in solvent and supporting electrolyte-free conditions. Green Chem. 2007, 9, 323-325.
32. For recent contributions see references 29-32 : Saha, P.; Naskar, S.; Paira, P.; Hazra, A.; Sahu, K.B.; Paira, R.; Banerjee, S.; Mondal, N.B. Basic alumina-supported highly effective Suzuki-Miyaura cross-coupling reaction under microwave irradiation: Application to fused tricyclic oxa-aza-quinolones. Green Chem. 2009, 11, 931-934.
33. Góra, M.; Kozik, B.; Jamrozy, K.; Luczynski, M.L.; Brzuzan, P.; Wozny, M. Solvent-free condensations of ketones with malononitrile catalysed by methanesulfonic acid/morpholine system. Green Chem. 2009, 11, 863-867.
34. Trotzki, R.; Hoffmann, M.H.; Ondruschka, B. Highly enantioselective hydrogenation of quinolines under solvent-free or highly concentrated conditions. Green Chem. 2009, 11, 767-769.
35. Clavino-Casilda, V.; Guerrero-Pérez, M.O.; Bañares, M.A. Efficient microwave-promoted acrylonitrile sustainable synthesis from glycerol. Green Chem. 2009, 11, 939-941.
36. For reviews see references 33-36: Kappe, C.O. Controlled microwave heating in modern organic synthesis. Angew. Chem. Int. Ed. 2004, 43, 6250-6284.
37. Bougrin, K.; Loupy, A.; Soufiaoui, M. Microwave-assisted solvent-free heterocyclic synthesis. J. Photochem. Photobiol. C. Photochem. Rev. 2005, 6, 139-169.
38. Bougrin, K.; Soufiaoui, M.; Bashiardes, G. Microwaves in cycloadditions. In Microwaves in Organic Synthesis, 2nd ed.; Loupy, A., Ed.; Wiley-VCH: Weinheim, Germany, 2006; Volume 2, pp. 524-578.
39. Kappe, C.O.; Dallinger, D. Controlled microwave heating in modern organic synthesis: Highlights from the 2004-2008 literature. Mol. Divers. 2009, 13, 71-193.
40. Bougrin, K.; Loupy, A.; Petit, A.; Daou, B.; Soufiaoui, M. Nouvelle voie de synthèse des 2-trifluorométhylarylimidazoles sur montmorillonite K10 en milieu sec sous micro-onde. Tetrahedron 2001, 57, 163-168.
41. Mallouk, S.; Bougrin, K.; Doua, H.; Benhida, R.; Soufiaoui, M. Ultrasound-accelerated aromatisation of trans- and cis-pyrazolines under heterogeneous conditions using claycop. Tetrahedron 2004, 45, 4143-4148.
42. Guezguez, R.; Bougrin, K.; El-Akri, K.; Benhida, R. A highly efficient microwave-assisted solvent-free synthesis of α- and β-2'-deoxy-1,2,3- triazolyl-nucleosides. Tetrahedron. Lett. 2006, 47, 4807-4811.
43. El-Akri, K.; Bougrin, K.; Balzarini, J.; Faraj, R.; Benhida, R. Efficient synthesis and in vitro cytostatic activity of 4-substituted triazolyl-nucleosides. Tetrahedron. Lett. 2007, 17, 6656-6659.
44. EL-Hammari, L.; Laghzizil, A.; Barboux, P.; Saoiabi, A.; Lahlil, K. Crystallinity and fluorine substitution effects on the proton conductivity of porous hydroxyapatites. J. Solid-State Chem. 2004, 177, 134-138.
45. For review on thermal and non-thermal microwave effects see: De La Hoz, A.; Diaz-Ortiz, A.; Moreno, A. Microwaves in organic synthesis. Thermal and non-thermal microwave effects. Chem. Soc. Rev. 2005, 164-178.
46. Tierney, J.P.; Lidström, P. Microwave Assisted Organic Synthesis; Blackwell: Oxford, UK, 2005.