A Novel Cu-catalysed Three-component One-pot Synthesis of Dihydropyrimidin-2(1H)-ones Using Microwaves under Solvent-free Conditions

Synlett

Volumn , Issue 2, 2004, Pages 235-238

  Gohain, Mukut ^a   Prajapati, Dipak ^a   Sandhu, Jagir S ^b  

^a REGIONAL RESEARCH LABORATORY   (India)

^b PUNJABI UNIVERSITY   (India)

Author keywords

Biginelli condensation; Cupric chloride; Cupric sulphate; Dihydropyrimidinones; Three component reactions

Indexed keywords

ALDEHYDE; BETA OXOCARBOXYLIC ACID ESTER; COPPER; CUPRIC CHLORIDE; ESTER; HYDROXYL GROUP; PYRIMIDINE DERIVATIVE; SOLVENT; THIOUREA; UNCLASSIFIED DRUG; UREA;

ARTICLE; CATALYSIS; CATALYST; DRUG SYNTHESIS; MICROWAVE RADIATION; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; MOLECULAR MECHANICS; POLYMERIZATION; REACTION ANALYSIS; ROOM TEMPERATURE; SUBSTITUTION REACTION; SYNTHESIS; TECHNIQUE;

EID: 1242341296     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-43374     Document Type: Article

References (53)

1. (a) Biginelli, P. Gazz. Chim. Ital. 1893, 23, 360.
2. (b) Kappa, C. O. Tetrahedron 1993, 49, 6937.
3. (c) Kappe, C. O. Acc. Chem. Res. 2000, 33, 879.
4. (d) Wipf, P.; Cunningham, A. Tetrahedron Lett. 1995, 36, 7819.
5. (e) Studer, A.; Jeger, P.; Wipf, P.; Curran, D. P. J. Org. Chem. 1997, 62, 2917.
6. (a) Atwal, K. S.; Swanson, B. N.; Unger, S. E.; Floyd, D. M.; Moreland, S.; Hedberg, A.; O'Reilly, B. C. J. Med. Chem. 1991, 34, 806.
7. (b) Rovnyak, G. C.; Kimball, S. D.; Beyer, B.; Cucinotta, G.; DiMarco, J. D.; Gougoutas, J.; Hedberg, A.; Malley, M.; McCarthy, J. P.; Zhang, R.; Moreland, S. J. J. Med. Chem. 1995, 38, 119.
8. (c) Rovnyak, G. C.; Atwal, K. S.; Hedberg, A.; Kimball, S. D.; Moreland, S.; Gougoutas, J. Z.; O'Reilly, B. C.; Schwartz, J.; Malley, M. F. J. Med. Chem. 1992, 35, 3254.
9. (d) Kappe, C. O.; Fabian, W. M. F.; Semones, M. A. Tetrahedron 1997, 53, 2803.
10. Overman, L. E.; Rabinowitz, M. H.; Renhowe, P. A. J. Am. Chem. Soc. 1995, 117, 2657.
11. (a) Patil, A. D.; Kumar, N. V.; Kokke, W. C.; Bean, M. F.; Freyer, A. J. ; DeBrosse, C.; Mai, S.; Truneh, A.; Faulkner, D. J.; Carte, B.; Breen, A. L.; Hertzberg, R. P.; Johnson, R. K.; Westley, J. W.; Ports, B. C. M. J. Org. Chem. 1995, 60, 1182.
12. (b) Snider, B. B.; Chen, J.; Patil, A. D.; Freyer, A. J. Tetrahedron Lett. 1996, 37, 6977.
13. (c) Rama Rao, A. V.; Gurjar, M. K.; Vasudevan, J. J. Chem. Soc., Chem. Commun. 1995, 1369.
14. (a) Zavyalov, S. I.; Kulikova, L. B. Khim.-Fam. Zh. 1992, 26, 116.
15. (b) Gupta, R.; Gupta, A. K.; Paul, S.; Kachroo, P. L. Indian J. Chem., Sect. B 1995, 34, 151.
16. (c) Hu, E. H.; Sidler, D. R.; Dolling, U. H.; Patane, M. A. PCT Int. Appl. WO 97 21,687, 1997; Chem. Abstr. 1997, 127, 121750v.
17. For a study of the pH dependence of the reaction see: Ehsan, A.; Karimullah, Pak. J. Sci. Ind. Res. 1967, 10, 83.
18. (a) O'Reilly, B. C.; Atwal, K. S. Heterocycles 1987, 26, 1185.
19. (b) Atwal, K. S.; O'Reilly, B. C.; Gougoutas, J. Z.; Malley, M. F. Heterocycles 1987, 26, 1189.
20. (c) Shutalev, A. D.; Kuksa, V. A. Khim. Geterotsikl. Soedin. 1997, 105.
21. (d) Shutlev, A. D.; Kishko, E. A.; Sivova, N. V.; Kuznetsov, A. Y. Molecules 1998, 3, 100.
22. Hu, E. H.; Sidler, D. R.; Dolling, U. H. J. Org. Chem. 1998, 63, 3454.
23. Bigi, F.; Carloni, S.; Frullanti, B.; Maggi, R.; Sartori, G. Tetrahedron Lett. 1999, 40, 3465.
24. Ranu, B. C.; Hajra, A.; Jana, U. J. Org. Chem. 2000, 65, 6270.
25. Yadav, J. S.; Reddy, B. V. S.; Reddy, K. B.; Raj, K. S.; Prasad, A. R. J. Chem. Soc., Perkin Trans. 1 2001, 1939.
26. Ma, Y.; Qian, C.; Wang, L.; Yang, M. J. Org. Chem. 2000, 65, 3864.
27. (a) Kappe, C. O.; Falsome, S. F. Synlett 1998, 718.
28. (b) Kumar, K. A.; Kasthuraiah, M.; Reddy, C. S.; Reddy, C. D. Tetrahedron Lett. 2001, 42, 7873.
29. 2O see: Subhas Bose, D.; Fatima, L.; Mereyala, H. B. J. Org. Chem. 2003, 68, 587.
30. 2 see: Paraskar, A. S.; DewKar, G. K.; Sudalai, A. Tetrahedron Lett. 2003, 44, 3305.
31. 3SiI see: Sabitha, G.; Reddy, G. S. K. K.; Reddy, C. S.; Yadav, J. S. Synlett 2003, 858.
32. (d) Using silicasulfuric acid see: Salehi, P.; Dabiri, M.; Zolfigol, M. A.; Bodagh Ford, M. A. Tetrahedron Lett. 2003, 44, 2889.
33. (e) Using LiBr see: Baruah, P. P.; Gadhwal, S.; Prajapati, D.; Sandhu, J. S. Chem. Lett. 2002, 1038.
34. (f) See also: Maiti, G.; Kundu, P.; Guin, C. Tetrahedron Lett. 2003, 44, 2757.
35. (g) Using boric acid see: Tu, S.; Fang, F.; Miao, C.; Jiang, H.; Feng, Y.; Shi, D.; Wang, X. Tetrahedron Lett. 2003, 44, 6153.
36. 4 see: Reddy, C. V.; Mahesh, M.; Raju, P. V. K. ; Romeshbabu, T.; Reddy, V. V. N. Tetrahedron Lett. 2002, 43, 2657.
37. 3 see: Fu, N.; Yuan, Y.; Cao, Z.; Wang, S.; Wang, J.; Peppe, C. Tetrahedron 2002, 58, 4801.
38. (j) Using soluble polymer support see: Xia, M.; Wang, Y. Tetrahedron Lett. 2002, 43, 7703.
39. (k) Using HCl see: Kidwai, M.; Saxena, S.; Mohan, R.; Venkataramanan, R. J. Chem. Soc., Perkin Trans. 1 2002, 1845.
40. (l) Using ferric chloride see: Lu, J.; Bai, Y. Synthesis 2002, 46.
41. (m) Using ammonium chloride see: Shaabani, A.; Bazgir, A.; Teimouri, F. Tetrahedron Lett. 2003, 44, 857.
42. (a) Singh, K.; Singh, J.; Deb, P. K.; Singh, H. Tetrahedron 1999, 55, 12873.
43. (b) Lu, J.; Ma, H. Synlett 2000, 63.
44. Atwal, K. S.; Rovnyak, G. C.; O'Reilly, B. C.; Schwartz, J. J. Org. Chem. 1989, 54, 5898.
45. (a) Cossy, J.; Willis, C.; Bellosta, V.; Saint-Jalmes, L. Synthesis 2002, 951.
46. (b) Pourashraf, M.; Delair, P.; Rasmussen, M. O.; Greene, A. E. J. Org. Chem. 2000, 65, 6966.
47. Folkers, K.; Harwood, H. J.; Johnson, T. B. J. Am. Chem. Soc. 1932, 54, 3751.
48. (a) Mayer, T. U.; Kapoor, T. M.; Haggarty, S. J.; King, R. W.; Schreiber, S. L.; Mitchison, T. J. Science 1999, 286, 971.
49. (b) Dondoni, A.; Massi, A.; Sabbatini, S. Tetrahedron Lett. 2002, 43, 5913.
50. Eynde, J. J. V.; Audiart, N.; Canonne, V.; Michel, S.; Haverbeke, Y. V.; Kappe, C. O. Heterocycles 1997, 45, 1967.
51. Kappe, C. O. J. Org. Chem. 1997, 62, 7201.
52. (a) Kappe, C. O.; Kumar, D.; Varma, R. S. Synthesis 1999, 1799.
53. (b) Yadav, J. S.; Reddy, B. V. S.; Srinivas, R.; Venugopal, C.; Ramalingam, T. Synthesis 2001, 1341.