Microwave-mediated Biginelli reactions revisited. On the nature of rate and yield enhancements

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 7, 2000, Pages 1363-1368

  Stadler, Alexander ^a   Kappe, C Oliver ^a  

^a UNIVERSITY OF GRAZ   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CHEMICAL REACTORS; CONDENSATION; ETHANOL; MICROWAVE HEATING; MIXTURES; ORGANIC SOLVENTS; PRESSURE EFFECTS; RATE CONSTANTS; SOLUTIONS; THERMAL EFFECTS; UREA;

ARYL ALDEHYDE; DIHYDROPYRIMIDINE; MICROWAVE-MEDIATED BIGINELLI REACTION; THERMAL HEATING; THIOUREA;

SYNTHESIS (CHEMICAL);

EID: 0034236727     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/b002697m     Document Type: Article

References (49)

1. (a) R. A. Abramovitch, Org. Prep. Proced. Int., 1991, 23, 685
2. (b) D. R. Baghurst and D. M. P. Mingos, Chem. Soc. Rev., 1991, 20, 1
3. (c) R. N. Gedye, F. E. Smith and K. C. Westaway, J. Microwave Power Electromagn. Energy, 1991, 26, 3
4. (d) G. Majetich and R. Hicks, Res. Chem. Intermed., 1994, 20, 61
5. (e) S. Caddick, Tetrahedron, 1995, 51, 10403
6. (f) C. R. Strauss and R. W. Trainor, Aust. J. Chem., 1995, 48, 1665
7. (g) G. Majetich and R. Hicks, Radiat. Phys. Chem., 1995, 45, 567.
8. (a) K. C. Westaway and R. N. Gedye, J. Microwave Power Electromagn. Energy, 1995, 30, 219
9. (b) J. Jacob, L. H. L. Chia and F. Y. C. Boey, J. Mater. Sci., 1995, 30, 5321
10. (c) F. Langa, P. de la Cruz, A. de la Hoz, A. Díaz-Ortiz and E. Díez-Barra, Contemp. Org. Synth., 1997, 4, 373
11. (d) S. L. Cresswell and S. J. Haswell, Chem. Ind., 1999, 621
12. (e) R. Dagani, Chem. Eng. News, 1997, February 10 issue, p. 26.
13. (a) A. K. Bose, B. K. Banik, N. Lavlinskaia, M. Jayaraman and M. S. Manhas, CHEMTECH, 1997, 27, 18
14. (b) S. A. Galema, Chem. Soc. Rev., 1997, 26, 233
15. (c) C. Gabriel, S. Gabriel, E. H. Grant, B. S. J. Halstead and D. M. P. Mingos, Chem. Soc. Rev., 1998, 27, 213
16. (d) C. R. Strauss, Aust. J. Chem., 1999, 52, 83.
17. (a) A. Loupy, A. Petit, J. Hamelin, F. Texier-Boullet, P. Jacquault and D. Mathé, Synthesis, 1998, 1213
18. (b) R. S. Varma, Green Chem., 1999, 43
19. (c) R. S. Varma, Clean Prod. Process., 1999, 1, 132
20. (d) R. S. Varma, K. P. Naicker, D. Kumar, R. Dahiya and P. J. Liesen, J. Microwave Power Electromagn. Energy, 1999, 34, 113.
21. S. Deshayes, M. Liagre, A. Loupy, J.-L. Luche and A. Petit, Tetrahedron, 1999, 55, 10851.
22. (a) R. N. Gedye and J. B. Wei, Can. J. Chem., 1998, 76, 525
23. (b) R. Laurent, A. Laporterie, J. Dubac, J. Berlan, S. Lefeuvre and M. Audhuy, J. Org. Chem., 1992, 57, 7099
24. (c) P. Goncalo, C. Roussel, J. M. Milot and J. Vébrel, J. Chem. Soc., Perkin Trans. 2, 1999, 2111
25. R. Gupta, A. K. Gupta, S. Paul and P. L. Kachroo, Ind. J. Chem., 1995, 34B, 151.
26. A. Dandia, M. Saha and H. Taneja, J. Fluorine Chem., 1998, 90, 17.
27. P. Biginelli, Gazz. Chim. Ital., 1893, 23, 360.
28. C. O. Kappe, Tetrahedron, 1993, 49, 6937.
29. (a) C. O. Kappe, J. Org. Chem., 1997, 62, 7201
30. (b) C. O. Kappe, S. F. Falsone, W. M. F. Fabian and F. Belaj, Heterocycles, 1999, 51, 77.
31. (a) E. H. Hu, D. R. Sidler and U.-H. Dolling, J. Org. Chem., 1998, 63, 3454
32. (b) C. O. Kappe and F. S. Falsone, Synlett, 1998, 718
33. (c) F. Bigi, S. Carloni, B. Frullanti, R. Maggi and G. Sartori, Tetrahedron Lett., 1999, 40, 3465
34. (d) K. Singh, J. Singh, P. K. Deb and H. Singh, Tetrahedron, 1999, 55, 12873.
35. For the description of a prototype of this reactor, see: (a) K. D. Raner, C. R. Strauss, R. W. Trainor and J. S. Thorn, J. Org. Chem., 1995, 60, 2456
36. (b) A. Schmaling, M. Metzger and M. Loechner, Am. Lab., July 1998, 37
37. (a) K. Folkers, H. J. Harwood and T. B. Johnson, J. Am. Chem. Soc., 1932, 54, 3751
38. (b) K. Folkers and T. B. Johnson, J. Am. Chem. Soc., 1933, 55, 3785
39. (c) K. Folkers and T. B. Johnson, J. Am. Chem. Soc., 1933, 55, 2886.
40. K. Atwal, B. C. O'Reilly, J. Z. Gougoutas and M. F. Malley, Heterocycles, 1987, 26, 1189.
41. D. R. Baghurst and D. M. P. Mingos, J. Chem. Soc., Chem. Commun., 1992, 674.
42. R. Saillard, M. Poux, J. Berlan and M. Audhuy-Peaudecerf, Tetrahedron, 1995, 51, 4033.
43. D. M. P. Mingos, Res. Chem. Intermed., 1994, 20, 85.
44. D. M. Stout and A. J. Myers, Chem. Rev., 1982, 82, 223.
45. H. M. Kingston, P. J. Walter, W. G. Engelhart and P. J. Parsons, in Microwave-Enhanced Chemistry; eds. H. M. Kingston and S. J. Haswell, American Chemical Society, Washington, 1997, Ch. 16, p. 697.
46. (a) C. O. Kappe, D. Kumar and R. S. Varma, Synthesis, 1999, 1799
47. (b) R. Gupta, S. Paul and K. Gupta, Ind. J. Chem. Technol., 1998, 5, 340.
48. Milestone Inc., 160B Shelton Road, Monroe, CT 06468, USA; phone: +1-203-261-6175; fax: +1-203-261-6592; e-mail: mwave@milestonesci.com.
49. J. J. Vanden Eynde, F. Delfosse, A. Mayence and Y. VanHaverbeke, Tetrahedron, 1995, 51, 6511.