An Efficient Knoevenagel Condensation Catalyzed by LaCl3.7H 2O in Heterogeneous Medium

Synthetic Communications

Volumn 33, Issue 21, 2003, Pages 3825-3832

  Narsaiah, A Venkat ^a   Nagaiah, K ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Active methylene compounds; Knoevenagel condensation; Lanthanum chloride; Substituted alkenes; Trimethoprim

Indexed keywords

ALDEHYDE DERIVATIVE; ALKENE; CARBENE; LANTHANUM CHLORIDE; LEWIS ACID; SOLVENT; WATER;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; HEATING; POLYMERIZATION; SYNTHESIS; TEMPERATURE DEPENDENCE;

EID: 0242299677     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120025194     Document Type: Article

References (24)

1. Knoevenagel, E. Condensationen zwischen malonester und aldehyden unter dem einfluss von ammoniak und organischen amminen. Chem. Ber. 1898, 31, 2596.
2. (a) Jones, G. Organic Reactions; The Knoevenagel condensation reaction, Wiley: New York, 1967; Vol. XV, 204 p;
3. (b) Popp, F.D.; McEwen, W.E. Chem. Rev. 1958, 58, 321.
4. (a) Rao, P.S.; Venkataratnam, R.V. Zinc chloride as a new catalyst for Knoevenagel condensation. Tetrahedron Lett. 1991, 32, 5821;
5. 4/THF/pyridine (I). Tetrahedron Lett. 1970, 54, 4723.
6. (a) Texier-Boullet, F.; Foucaud, A. Knoevenagel condensation catalysed by aluminium oxide. Tetrahedron Lett. 1982, 23, 4927;
7. (b) Chalais, S.; Laszlo, P.; Mathy, A. Catalysis of the Knooevenagel condensation. Tetrahedron Lett. 1985, 26, 4453;
8. (c) Cabello, J.A.; Campelo, J.M.; Garcia, A.; Luna, D.; Marinas, J.M. J. Org. Chem. 1984, 49, 5195;
9. (d) Bram, G.; Loupy, A.; Villemin, D. In Solid Supports and Catalyst in Organic Synthesis; Smith, K., 1992, Ellis Horwood, Prentice Hall: Chichester, 1992; Ch. 12;
10. (e) Villemin, D.; Martin, B. J. Chem. Res. (S) 1994, 146;
11. (f) Angeletti, E.; Canepa, C.; Martinetti, G.; Venturello, P. Amino groups immobilized on Silica gel; An efficient and reusable heterogeneous catalyst for the Knoevenagel condensation. J. Chem. Soc. Perkin Trans. 1, 1989, 105;
12. (g) Abdallah-E, Ayobbis, S.; Texier-Boullet, F. J. Chem. Res. (S) 1995, 208;
13. (h) Cruz, P.D.L.; Barra, D.E.; Loupy A.; Lang, F. Silica gel catalysed Knoevenagel condensation in dry media under microwave irradiation. Tetrahedron Lett. 1996, 37, 1113;
14. (i) 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;
15. (j) Reddy, T.I.; Varma, R.S. Rare-earth (RE) exchanged NaY zeolite promoted Knoevenagel condensation. Tetrahedron Lett. 1997, 38, 1721;
16. (k) Franca, B.; Luca, C.; Raimondo, M.; Giovanni, S. 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.
17. Luche, J.L.; Gemal, A.L. Efficient synthesis of acetals catalysed by rare earth Chlorides. J. Chem. Soc., Chem. Commun. 1978, 976.
18. Gomal, A.L.; Luche, J.L. Lanthanoids in organic synthesis. 6. The reducation of α-enones by sodium borohydride in the presence of lanthanoid chlorides: Synthetic and Mechanistic Aspects. J. Amer. Chem. Soc. 1981, 103, 5454.
19. Fukuzawa, S.; Fujinami, J.; Yamauchi, S.; Sakai, S. 1,2-Reioselective reduction of α,β-unsaturated carbonyl compounds with lithium aluminium hydride in the presence of lanthanoid salts. J. Chem. Soc. Perkin Trans 1. 1986, 1929.
20. 13C-enriched 2,4-Diamines-5-(3,4,5-trimethoxy benzyl) pyrimidine (trimethoprim) and 2,4-diaminopyrimidine. J. Chem. Soc. Perkin Trans 1. 1986, 747.
21. (a) Roth, B.; Falco, E.A.; Hitchings, G.H.; Bushby, S.R.M. J. Med. Pharm. Chem. 1962, 5, 1103;
22. (b) Sebti, S.; Nazih, R.; Rahir, R.; Salhi, L.; Saber, H. Fluorapatite: new solid catalyst of the Knoevenagel reaction in heterogenous media with solvent. Applied Catalysis A 2000, 197, L187-L190.
23. (a) Curini, M.; Francesco, E.; Maria, C.M.; Orneli, R.; Andre, T.; Potassium exchanged layered zirconium phosphate as base catalyzed in Knoevenagel condensation. Synthetic Communi. 2002, 33 (3), 355-362;
24. (b) Sang-Yun, Y.K.; Pan-Suk, K.; Tae-Woo, Kwon. Microwave enhanced Knoevenagel condensation of ethyl cyano acetate with aldehydes. Synthetic Communi. 1997, 27 (4), 533-541.