Efficient synthesis of chalcones by a solid base catalyst

Synthetic Communications

Volumn 35, Issue 14, 2005, Pages 1971-1978

  Kantam, M Lakshmi ^a   Veda Prakash, B ^a   Venkat Reddy, Ch ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Arylaldehydes; Chalcones; Hydrotalcites; Solid base

Indexed keywords

ALDEHYDE; ALUMINUM; CHALCONE DERIVATIVE; HYDROTALCITE; KETONE DERIVATIVE; MAGNESIUM;

ARTICLE; CATALYST; CLAISEN CONDENSATION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; SOLID STATE; STRUCTURE ANALYSIS;

EID: 22144457037     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200065006     Document Type: Article

References (25)

1. Tomazela, D. M.; Pupo, M. T.; Passador, E. A. P.; da Silva, M. F. G. F.; Vieira, P. C.; Fernandes, J. B.; Rodrigues, F. E.; Oliva, G.; Pirani, J. R. Pyrano chalcones and a flavone from Neoraputia magnifica and their Trypanosoma cruzi glycosomal glyceraldehyde-3-phosphate dehydrogenase-inhibitory activities. Phytochemistry 2000, 55 (6), 643.
2. (a) Wattenberg, L. W.; Coccia, J. B.; Galbraith, A. R. Inhibition of carcinogen-induced pulmonary and mammary carcinogenesis by chalcone administered subsequent to carcinogen exposure. Cancer Lett. 1994, 83 (1), 165;
3. (b) Dinkova-Kostova, A. T.; Abeygunawardana, C.; Talalay, P. Chemoprotective properties of phenylpropenoids, bis(benzylidene)cycloalkanones, and related Michael reaction acceptors: Correlation of potencies as phase 2 enzyme inducers and radical scavengers. J. Med. Chem. 1998, 41 (26), 5287.
4. Ram, V. J.; Saxena, A. S.; Srivastava, S.; Chandra, S. Oxygenated chalcones and bischalcones as potential antimalarial agents. Bioorg. Med. Chem. Lett. 2000, 10 (19), 2159.
5. Kidwai, M.; Sapra, P.; Misra, P.; Saxena, R. K.; Singh, M. Microwave-assisted solid support synthesis of novel 1,2,4-triazolo[3,4-b]-1,3,4- thiadiazepines as potent antimicrobial agents. Bioorg. Med. Chem. 2001, 9 (2), 217.
6. Ballesteros, J. F.; Sanz, M. J.; Ubeda, A.; Miranda, M. A.; Iborra, S.; Paya, M.; Alcaraz, M. J. Synthesis and pharmacological evaluation of 2′-hydroxychalcones and flavones as inhibitors of inflammatory mediators generation. J. Med. Chem. 1995, 38 (14), 2794.
7. (a) Harbone, J. B.; Mabry, T. J.; Mabry, H. The Flavonoids; Academic Press: New York, 1976;
8. (b) Harbone, J. B.; Mabry, T. J. The Flavonoids: Advances in Research; Chapman & Hall: New York, 1982;
9. Drexler, M. T.; Amiridis, M. D. The effect of solvents on the heterogeneous synthesis of flavanone over MgO. J. Catal. 2003 (214), 136.
10. Dhar, D. N. The Chemistry of Chalcones and Related Compounds; Wiley: New York, 1981.
11. Varma, R. S.; Kabalka, G. W.; Evans, L. T.; Pagni, R. M. Aldol condensations on basic alumina: The facile synthesis of chalcones and enones in a solvent-free medium. Synth. Commun. 1985, 15 (4), 279.
12. Sinisterra, J. V.; Garcia-Raso, A.; Cabello, J. A.; Marinas, J. M. An improved procedure for the Claisen-Schmidt reaction. Synthesis 1984, 502.
13. (a) Climent, M. J.; Corma, A.; Iborra, S.; Primo, J. Base catalysis for fine chemicals production: Claisen-Schmidt condensation on zeolites and hydrotalcites for the production of chalcones and flavanones of pharmaceutical interest. J. Catal. 1995, 151 (1), 60;
14. (b) Climent, M. J.; Corma, A.; Iborra, S.; Velty, A. Activated hydrotalcites as catalysts for the synthesis of chalcones of pharmaceutical interest. J. Catal. 2004, 221 (2), 474 and references cited therein.
15. (a) Sebti, S.; Solhy, A.; Tahir, R.; Boulaajaj, S.; Mayoral, J. A.; Fraile, J. M.; Kossir, A.; Oumimoum, H. Calcined sodium nitrate/natural phosphate: An extremely active catalyst for the easy synthesis of chalcones in heterogeneous media. Tetrahedron Lett. 2001, 42 (45), 7953;
16. (b) Sebti, S.; Solhy, A.; Tahir, R.; Abdelatif, S.; Boulaajaj, S.; Mayoral, J. A.; Garcia, J. I.; Fraile, J. M.; Kossir, A.; Oumimoum, H. Application of natural phosphate modified with sodium nitrate in the synthesis of chalcones: A soft and clean method. J. Catal. 2003, 213 (1), 1.
17. Choudary, B. M.; Lakshmi Kantam, M.; Venkat Reddy, Ch.; Bharathi, B.; Figueras, F. Wadsworth-Emmons reaction: The unique catalytic reaction by a solid base. J. Catal. 2003, 218 (1), 191 and references cited therein.
18. Pouchert, C. J. The Aldrich Library of NMR Spectra, Vol. 2, 54B, Miluwaukee: Aldrich Chemical Society Inc., 1983.
19. Boven, P. J.; Robinson, T. P.; Ehlers, T.; Goldsmith, D.; Arbisar, J. Chalcones and its analogs as agents for the inhibition of angiogenesis and related disease states. PCT, WO 01/46110 A2, Atlanta: University of Georgia Research Foundation, 2001.
20. Ishikawa, T.; Mizuta, T.; Hagiwara, K.; Aikawa, T.; Kudo, T.; Saito, S. Catalytic alkynylation of ketones and aldehydes using quaternary ammonium hydroxide base. J. Org. Chem. 2003, 68 (9), 3702.
21. Powers, D. G.; Casebier, D. S.; Fokas, D.; Ryan, W. J.; Troth, J. R.; Coffen, D. L. Automated parallel synthesis of chalcone-based screening libraries. Tetrahedron 1998, 54, 4085.
22. Salehi, P.; Khodaei, M. M.; Zolfigol, M. A.; Keyvan, A. Solvent-free crossed aldol condensation of ketones with aromatic aldehydes mediated by magnesium hydrogensulfate. Monatsh. Chem. 2002, 133, 1291.
23. Lopez, S. N.; Castelli, M. V.; Zacchino, S. A.; Domínguez, J. N.; Lobo, G.; Charris-Charris, J.; Cortes, J. C. G.; Ribas, J. C.; Devia, C.; Rodríguez, A. M.; Enriz, R. D. In vitro antifungal evaluation and structure-activity relationships of a new series of chalcone derivatives and synthetic analogues, with inhibitory properties against polymers of the fungal cell wall. Bioorg. Med. Chem. 2001, 9, 1999.
24. Applequist, D.; Gdanski, R. D. Kinetic study of the homolytic brominolysis of 1,2-diarylcyclopropanes. J. Org. Chem. 1981, 46, 2502.
25. Carde, L.; Davies, D. H.; Roberts, S. M. Stereocontrolled ring-opening of some enantiomerically enriched epoxy ketones and epoxy alcohols using trimethyl-aluminium: Synthesis of (S)-2-arylpropanoic acids. J. Chem. Soc., Perkin Trans. 1 2000 (15), 2455.