Rapid and cleaner synthesis of 1,4-dihydropyridines in aqueous medium

Heteroatom Chemistry

Volumn 17, Issue 4, 2006, Pages 267-271

  Sivamurugan, V ^a   Vinu, A ^b   Palanichamy, M ^a   Murugesan, V ^a  

^a ANNA UNIVERSITY   (India)

^b NATIONAL INSTITUTE FOR MATERIALS SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; DERIVATIVES; IRRADIATION; MICROWAVES; RECYCLING; SEPARATION; SOLUBILITY; SOLUTIONS;

ACID COMPLEX; AQUEOUS MEDIA; METHODOLOGY; MICROWAVE POWER;

NITROGEN COMPOUNDS;

EID: 33744490093     PISSN: 10427163     EISSN: 10981071     Source Type: Journal    
DOI: 10.1002/hc.20197     Document Type: Article

References (37)

1. Lindstrom, U. M. Chem Rev 2004, 102, 2751.
2. (a) Breslow, R.; Maitra, U. Tetrahedron Lett 1984, 25, 1239;
3. (b) Grieco, P. A.; Yoshida, R.; Garner, P. J Org Chem 1983, 48, 3137.
4. Gajewsky, J. J. Ace Chem Res 1997, 30, 219.
5. Kobayashi, S. In Organic Synthesis in Water; Grieco, P. A. (Ed.); Blackie Academic & Professional: London, 1998.
6. (a) Lu, W.; Chan, T. H. J Org Chem 2001, 66, 3467;
7. (b) Loh, T. P.; Zhou, J. R. Tetrahedron Lett 1999, 40, 9115.
8. Fokin, V. V.; Sharpless, K. B. Angew Chem Int Ed Engl 2001, 40, 3455.
9. Nagel, U.; Albrecht, J. Top Catal 1998, 5, 3.
10. Loev, B.; Goodman, M. M.; Snader, K. M.; Tedeschi, R.; Macko, E. J Med Chem 1974, 19, 956.
11. Liang, J.-C.; Yeh, J.-L.; Wang, C.-S.; Liou, S.-E; Tsai, C.-H.; Chen, I. J. Bioorg Med Chem 2002, 10, 719.
12. Hantzsch, A. Justus Liebigs Ann Chem 1882, 215, 1.
13. Sausins, H.; Duburs, G. Heterocycles 1988, 27, 269.
14. Gordeev, M. F.; Patel, D. V.; Gordon, E. M. J Org Chem 1996, 61, 924.
15. Breitenbucher, J. G.; Figliozzi, G. Tetrahedron Lett 2000, 41, 4311.
16. Ohberg, L.; Westman, J. Synlett 2001, 1296.
17. Anderson, G. J.; Berkelhammer, G. J Am Chem Soc 1958, 80, 992.
18. Phillips, P. J Am Chem Soc 1949, 71, 4003.
19. Maeyence, A. M.; Eynde, J.-J. V. Tetrahedron Lett 1991, 32, 3839.
20. Sabitha, G.; Reddy, G. S. K. K.; Reddy, Ch. S.; Yadav, J. S. Tetrahedron Lett 2003, 44, 4129.
21. Yadav, J. S.; Reddy, B. V. S.; Reddy, P. T. Synth Commun 2001, 31, 425.
22. Anniyappan, M.; Muralidharan, D.; Perumal, P. T. Synth Commun 2002, 32, 659.
23. Balalaie, S.; Kowsari, E. Monatsh Chem 2001, 132, 1551.
24. Nomura, M.; Nakata, S.; Hamada, F. Nippon Kagaku Kaishi 2002, 141.
25. Tu, S.-J.; Gao, Y.; Yu, C.-X.; Shi, D.-Q. Chinese J Org Chem 2002, 22, 269.
26. Lavilla, R. J Chem Soc, Perkin Trans 1, 2002, 1141.
27. Kidwai, M.; Saxena, S.; Mohan, R.; Venkatraman, R. J Chem Soc, Perkin Trans 1, 2002, 1845.
28. Cotterill, C.; Usyatinsky, A. Y.; Arnold, J. M.; Clark, D. S.; Dordick, J. S.; Michels, P. C.; Khmelnitsky, Y. L. Tetrahedron Lett 1998, 39, 1117.
29. Rodriguez, H.; Reyes, O.; Suarez, M.; Garay, H. E.; Perez, R.; Cruz, L. J.; Verdecia, Y.; Martin, N.; Seoane, C. Tetrahedron Lett 2002, 43, 439.
30. Kostyuk, N.; Volochnyuk, D. M.; Lupiha, L. N.; Pinchuk, A. M.; Tolmachev, A. A. Tetrahedron Lett 2002, 43, 5423.
31. Correa, W. H.; Scott, J. L. Green Chem 2001, 3, 296.
32. Ohberg, L.; Westman, J. Synlett 2005, 1296.
33. Vanden Eynde, J. J.; Mayence, A. Molecules 2003, 8, 381.
34. Lidstrom, P.; Tierny, J.; Washy, B.; Westman, J. Tetrahedron 2001, 57, 9225.
35. Sivamurugan, V.; Deepa, K.; Palanichamy, M.; Murugesan, V. Synth Commun 2004, 34, 3833.
36. 2 complex in 20 mL of double distilled water and 5 mL of absolute ethanol (Scheme 1). The reaction mixture was taken in an open Erlenmeyer flask and irradiated using a household microwave oven (model: IFB 17PM 1S) with a power range of 200 W (≈75°C) and a pulse of 10 s. The progress of the reaction was monitored by TLC (silica gel precoated plate, eluent:n-hexane to ethyl acetate ratio = 80:20) up to disappearance of reactants. After completion of the reaction, the mixture was kept at 10-15°C for 24 h. The product slowly crystallized from aqueous phase and it was separated by simple nitration. The purification step was not required as the product was in pure form. The above-mentioned procedure was followed for all other reactions. The reaction time and yield for all the reactions are given in Table 1.
37. Catalyst Recycling Studies. 2-Furfuraldehyde (5 mmol), acetylacetone (11 mmol), and ammonium acetate (10 mmol) were thoroughly mixed with catalyst (0.2 mmol). The progress of reaction was monitored by TLC analysis. After completion of reaction, the reaction mixture was diluted with dichloromethane and recovered the catalyst by simple separation from aqueous phase and organic phase. The catalyst present in aqueous medium was used for the subsequent cycle. The same procedure was adopted for all recycling studies. The reaction time and yield for different cycles are presented in Table 2.