Microwave assisted synthesis of diosgenin esters of maleic and itaconic acids

Synthetic Communications

Volumn 38, Issue 12, 2008, Pages 1917-1925

  Martínez García, Ariel ^a   Martínez, Ricardo ^a  

^a UNIVERSITY OF HAVANA   (Cuba)

Author keywords

Diosgenin; Modified microwave reactor; Monoitaconate; Monomaleate

Indexed keywords

DIOSGENIN; ITACONIC ACID; MALEIC ACID;

ARTICLE; CHEMICAL STRUCTURE; ESTERIFICATION; INFRARED SPECTROSCOPY; MICROWAVE OVEN; NUCLEAR MAGNETIC RESONANCE; REACTION TIME; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

EID: 45749118776     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910801997520     Document Type: Article

References (29)

1. Brosa, C.; Miró, X. Synthesis of new brassinosteroids with epoxy functions: The effect on the regioselectivity of the Baeyer-Villiger reaction. Tetrahedron 1997, 53, 11347-11354.
2. Brosa, C.; Soca, L.; Terricabras, E.; Ferrer, J. C.; Alsina, A. New synthetic brassinosteroids: A 5α-hydroxy-6-ketone analog with strong plant growth promoting activity. Tetrahedron 1998, 54, 12337-12348.
3. Kohout, L.; Kasal, A.; Strnad, M. Pregnane-type brassinosteroids with a four-carbon ester functionality in position 20. Collect. Czech. Chem. Commun. 1996, 61, 930-940.
4. Kohout, L.; Slavikoba, B.; Strand, M. 17a-Oxa-17a-homobrassinosteroid analogues. Collect. Czech. Chem. Commun. 1998, 63, 646-654.
5. Iglesias-Arteaga, M. A.; Pérez Gil, R.; Pérez Martínez, C. S.; Coll Manchado, F. Spirostanic analogues of teasterone: Synthesis, characterization, and biological activity of laxogenin, (23S)-hydroxylaxogenin and 23-ketolaxogenin (23-oxolaxogenin). J. Chem. Soc., Perkin Trans. 2001, 3, 261-266.
6. Iglesias-Arteaga, M. A.; Pérez Gil, R.; Leliebre Lara, V.; Pérez Martínez, C. S.; Coll Manchado, F. Synthesis of (25 R)-2α,3α-epoxy-5α-spirostan-6,23-dione. Synth Commun. 1998, 28, 4387-4392.
7. Iglesias-Arteaga, M. A.; Pérez Gil, R.; Leliebre Lara, V.; Pérez Martínez, C. S.; Coll Manchado, F. Synthesis of (25 R)-2α,3α,26-trihydroxy-5α-furostan-6-one. Synth Commun. 1998, 28, 1779-1784.
8. Iglesias-Arteaga, M. A.; Peαrez Gil, R.; Leliebre Lara, V.; Peαrez Martiαnez, C. S.; Rosado, A.; Coll Manchado, F. Synthesis of (25 R)-3β,26-dihydroxy-5α-furostan-6-one. Synth Commun. 1998, 28, 1381-1386.
9. (a) Loupy, A. (Ed.). Microwaves in Organic Synthesis; Wiley-VCH: Weinheim, 2006;
10. (b) Kappe, C. O.; Stadler, A. Microwaves in Organic and Medicinal Chemistry; Wiley-VCH: Weinhiem, 2005;
11. (c) Lidström, P.; Tierney, J. P. (Eds.). Microwave-Assisted Organic Synthesis; Blackwell: Oxford, 2005;
12. (d) Hayes, B. L. Microwave Synthesis: Chemistry at the Speed of Light; CEM Publishing: Matthews, NC, 2002;
13. (e) Lidström, P.; Tierney, J.; Wathey, B.; Westman, J. Microwave assisted organic synthesis - A review. Tetrahedron 2001, 57, 9225-9283.
14. Hoogenboom, R.; Schubert, U. S. Microwave-assisted polymer synthesis: Recent developments in a rapidly expanding field of research. Macromol. Rapid Commun. 2007, 28, 368-386.
15. (a) de la Hoz, A.; Díaz-Ortiz, A.; Moreno, A. Microwaves in organic synthesis: Thermal and non-thermal microwave effects. Chem. Soc. Rev. 2005, 34, 164-178;
16. (b) Kappe, C. O. Controlled microwave heating in modern organic synthesis. Angew. Chem. Int. Ed. 2004, 43, 6250-6284.
17. Amore, K. M.; Leadbeater, N. E. Microwave-promoted esterification reactions: Optimization and scale-up. Macromol. Rapid Commun. 2007, 28, 473-477.
18. Villa, C.; Mariani, E.; Loupy, A.;Grippo, C.; Grossi, G. C.; Bargagna, A. Solvent-free reactions as green chemistry procedures for the synthesis of cosmetic fatty esters. Green Chem. 2003, 5, 623-626.
19. Villa, C.; Baldassari, S.; Gambaro, R.; Mariani, E.; Loupy, A. Eco-friendly methodologies for the synthesis of some aromatic esters, well-known cosmetic ingredients. Internat. J. Cosmetic Sci. 2005, 27, 11-16.
20. 1H NMR studies of 5β-cholestane-3α, 7β,12α ,25-tetrol. Steroids 1997, 62, 409-414.
21. Pollington, S. D.; Bond, G.; Moyes, R. B.; Whan, D. A.; Candlin, J. P.; Jennings, J. R. The influences of microwave on the rate of reaction of propan-1-ol with ethanoic acid. J. Org. Chem. 1991, 56, 1313-1314.
22. Raner, K. D.; Strauss, C. R. Influence of microwaves on the rate of esterification of 2,4,6-trimet hylbenzoic acid with 2-propanol. J. Org. Chem. 1992, 57, 6231-6234.
23. Roy, I.; Gupta, M. N. Non-thermal effects of microwaves on protease-catalyzed esterification and transesterification. Tetrahedron 2003, 59, 5431-5436.
24. Velmathi, S.; Nagahata, R.; Sugiyama, J. I.; Takeuchi, K. A rapid ecofriendly synthesis of poly(butylene succinate) by a direct polyesterification under microwave irradiation. Macromol. Rapid Commun. 2005, 26, 1163.
25. Nagahata, R.; Sano, D.; Suzuki, H.; Takeuchi, K. Microwave-assisted single-step synthesis of poly(lactic acid) by direct polycondensation of lactic acid. Macromol. Rapid Commun. 2007, 28, 437-442.
26. Kahn, M. G. C.; Konde, E.; Dossou, F.; Labaree, D. C.; Hochberg, R. B.; Hoyte, R. M. Microwave-enhanced nucleophilic fluorination in the synthesis of fluoropyridyl derivatives of [3,2-c]pyrazolo-corticosteroids, potential glucocorticoid receptor-mediated imaging agents. Bioorg. Med. Chem. Lett. 2006, 16, 3454-3458.
27. Tietze, L. F.; Wiegand, J. M.; Vock, C. Synthesis of enantiopure B-nor-steroids by multiple Pd-catalyzed transformations. J. Org. Chem. 2003, 687, 346-352.
28. Narasimhan, S.; Velmathi, S. Effect of microwaves in the chiral switching asymmetric Michael reaction. Molecules 2003, 8, 256-262.
29. Zhang, G.; Niu, A.; Peng, S; Jiang, M.; Tu, Y.; Li, M.; Wu, C. Formation of novel polymeric nanoparticles. Acc. Chem. Res.. 2001, 34, 249-256.