Tetra-n-butylammonium hydroxide (TBAH)-catalyzed Knoevenagel condensation: A facile synthesis of α-cyanoacrylates, α-cyanoacrylonitriles, and α-cyanoacrylamides

Synthetic Communications

Volumn 36, Issue 4, 2006, Pages 533-539

  Balalaie, Saeed ^a   Bararjanian, Morteza ^a  

^a K N TOOSI UNIVERSITY OF TECHNOLOGY   (Iran)

Author keywords

Active methylene compounds; Aldehydes; Alkenes; Knoevenagel condensation; Microwave irradiation; Tetra n butylammonium hydroxide

Indexed keywords

ACRYLAMIDE DERIVATIVE; AMMONIUM DERIVATIVE; CYANOACRYLATE DERIVATIVE; NITRILE;

ARTICLE; CATALYST; CHEMICAL REACTION; KNOEVENAGEL CONDENSATION; OLEFINATION; REACTION ANALYSIS; SUBSTITUTION REACTION;

EID: 31744446138     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910500385258     Document Type: Article

References (42)

1. Jones, G. The Knovenagel condensation reaction. In Organic Reactions; Wiley: New York, 1967; Vol. 15, p. 204.
2. (a) Tietze, L.; Beifuos, V. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon: Oxford, 1991; Vol. 2; Chapter 1.11, 341-392;
3. (b) Bigi, F.; Chesini, L.; Maggi, R. R.; Sartori, G. Montmorillonite KSF as an inorganic, water soluble, and reusable catalyst for the Knoevenagel synthesis of coumarin-3-carboxylic acids. J. Org. Chem. 1999, 64, 1033;
4. (c) Yu, N.; Aramini, J. M.; Germann, M. W.; Huang, Z. Tetrahedron Lett. 2000, 41, 6993;
5. (d) Balalaie, S.; Nemati, N. One-pot preparation of coumarins by Knoevenagel condensation in solvent-free condition under microwave irradiation. Heterocycl. Commun. 2001, 7, 67;
6. (e) Su, C.; Chen, Z. C.; Zheng, Q. G. Organic reactions in ionic liquids: Knoevenagel condensation catalyzed by ethylenediammonium diacetate. Synthesis 2003, 555.
7. (a) Allen, C. F. H.; Spangler, F. W. Org. Synth. Coll. 1955, III, 377;
8. (b) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. Amino acid-catalyzed direct asymmetric aldol reactions: A biomorganic approach to catalytic asymmetric carbon-carbon bond forming reactions. J. Am. Chem. Soc. 2001, 123, 5260;
9. (c) Groger, H.; Wilken, J. The application of L-proline as an enzyme mimic and further new asymmetric syntheses using small organic molecules as chiral catalysts. Angew. Chem. Int. Ed. Engl. 2001, 40, 529;
10. (d) Cardillo, G.; Fabbroni, S.; Gentilucci, L.; Gianotti, M.; Tolomelli, A. A straightforward method for the synthesis of alkylidene and arylidene malonates through proline-catalyzed Knoevenagel condensation. Synth. Commun. 2003, 33, 1587.
11. (a) Prajapati, D.; Lekhok, K. C.; Sandhu, J. S.; Ghosh, A. C. Lithium bromide as a new catalyst for carbon-carbon bond formation in the solid state. J. Chem. Soc. Perkin Trans. 1 1996, 959;
12. (b) Rao, P. S.; Ratnam, R. V. Zinc chloride as a new catalyst for Knoevenagel condensation. Tetrahedron Lett. 1991, 32, 5821;
13. 3·7H2O in heteregenous medium. Synth. Commun. 2003, 33, 3819.
14. Texier-Boullet, F.; Foucod, A. Knoevenagel condensation catalyzed by aluminium oxide. Tetrahedron Lett. 1982, 23, 4927.
15. 3 as a new catalyst. J. Org. Chem. 1984, 49, 5195.
16. (a) Loupy, A. Solvent-free reactions. Top. Curr. Chem. 1999, 206, 153;
17. (b) Laszlo, P. Catalysis of organic reactions by inorganic solids. Acc. Chem. Res. 1986, 19, 121.
18. (a) Rodriguez, I.; Iborra, S.; Corma, A.; Rey, F.; Jorda, J. L. MCM-14-quaternary organic tetraalkylammonium hydroxide composites as strong and stable Bronsted base catalysts. J. Chem. Soc., Chem. Commun. 1999, 593;
19. (b) Wang, Q. L.; Ma, Y.; Zuo, B. Knoevenagel condensation catalyzed by USY zeolite. Synth. Commun. 1997, 27, 4107.
20. (a) Kloetstra, K. R.; Bekkum, H. V. J. Chem. Soc., Chem. Commun. 1995, 1005;
21. (b) Wada, S.; Suzuki, H. Calcite and fluoride as catalyst for the Knoevenagel condensation of malononitrile and methyl cyanoacetate under solvent-free conditions. Tetrahedron Lett. 2003, 44, 399;
22. (c) Sebti, S.; Smahi, A. V.; Solhy, A. Natural phosphate doped with potassium fluoride and modified with sodium nitrate: Efficient catalysts for the Knoevenagel condensation. Tetrahedron Lett. 2002, 43, 1813;
23. (d) Inaki, Y.; Kajita, Y. H.; Ito, K.; Hattori, T. J. Chem. Soc., Chem. Commun. 2001, 2358;
24. (e) Siebenhaar, B.; Casagrande, B.; Studer, M.; Blaser, H.-U. Can. J. Chem. 2001, 79, 566.
25. (a) Ayoubi, S. A.; Texier-Boullet, F.; Hamelin, J. Minute synthesis of electrophilic alkenes under microwave irradiation. Synthesis 1994, 258;
26. (b) Ayoubi, S. A.; Texier-Boullet, F. Clay-mediated synthesis of gem-bis(alkoxycarbonyl)alkenes under microwave irradiation. J. Chem. Res. Synop. 1995, 208;
27. (c) Balalaie, S.; Nemati, N. Ammonium acetate - basic alumina-catalyzed Knoevenagel condensation under microwave irradiation and solvent-free condition. Synth. Commun. 2000, 30, 869 and references therein;
28. (d) Loupy, A.; Petit, A.; Hamelin, J.; Texier-Boullet, F.; Jacqualt, P.; Mathe, F. New solvent-free organic synthesis using focused microwave. Synthesis 1998, 1213;
29. (e) Varma, R. S. Solvent-free reactions under microwave irradiations. Green Chem. 1999, 1, 43;
30. (f) Kaupp, G.; Naimi-Jamal, M. R.; Schmeyers, J. Solvent-free Knoevenagel condensation and Michael addition in the solid state in the melt with quantitive yield. Tetrahedron 2003, 59, 3753.
31. (a) Hangarge, R. V.; Sonwane, S. A.; Jarikote, D. V.; Shingare, M. S. Water-mediated uncatalyzed facile synthesis of ylidenenitriles of 4-oxo-(4H)-1-benzopyran-3-carbaldehyde. Green Chem. 2001, 3, 310;
32. (b) Wang, S.; Ren, Z.; Cao, W.; Tong, W. The Knoevenagel condensation of aromatic aldehydes with malononitrile or ethyl cyanoacetate in the presence of CTMAB in water. Synth. Commun. 2001, 31, 673;
33. Ren, Z.; Cao, W.; Tong, W.; Jing, X. Synth. Commun. 2002, 32, 1947.
34. Yadav, J. S.; Reddy, B. S.; Basak, A. K.; Visali, B.; Narsaiah, A. V.; Nagaiah, K. Phosphane-catalyzed Knoevenagel condensation: A facile synthesis of α-cyanoacrylates and α-cyanoacrylonitriles. Eur. J. Org. Chem. 2004, 546.
35. Paquette, L. A. Encyclopedia of Reagents for Organic Synthesis. Wiley: New York, 1995; Vol. 7, p. 4735.
36. Chen, E. Y. Synth. Commun. 1983, 13, 927.
37. Rao, Y. K.; Nagarajan, M. Tetrahedron Lett. 1988, 29, 107.
38. Ryback, G. U.S. Pat. 4,855,512, Chem. Abstr. 1989, 110, 134 878r.
39. Saa, J. M.; Cava, P. M. J. Org. Chem, 1977, 42, 347.
40. Obrador, E.; Castro, M.; Tamariz, J.; Zepeda, G.; Miranda, R.; Delgde, F. Knoevenagel condensation in heterogenous phase catalyzed by IR irradiation and tonsil actisil FF. Synth. Commun. 1998, 28, 4649.
41. Corson, B. B.; Stoughton, R. W. J. Am. Chem. Soc. 1928, 50, 2825.
42. Mitra, A. K.; De, N.; Karchaudhuri, A. Synth. Commun. 1999, 29, 2731.