1,3-dichloro-5,5-dimethylhydantoin as a novel and efficient homogeneous catalyst in Biginelli reaction

Bulletin of the Korean Chemical Society

Volumn 31, Issue 11, 2010, Pages 3238-3240

  Hojati, Seyedeh Fatemeh ^a   Gholizadeh, Mostafa ^b   Haghdoust, Mahnaz ^a   Shafiezadeh, Fatemeh ^a  

^a HAKIM SABZEVARI UNIVERSITY   (Iran)

^b FERDOWSI UNIVERSITY OF MASHHAD   (Iran)

Author keywords

Dicarbonyl; 1,3 Dichloro 5,5 dimethylhydantoin; 3,4 Dihydropyrimidin 2(1H) one; Aldehyde; Homogeneous

Indexed keywords

1,3-DICHLORO-5,5-DIMETHYLHYDANTOIN; 3,4-DIHYDROPYRIMIDIN-2(1H)-ONE; BIGINELLI REACTION; CATALYTIC AMOUNTS; DIHYDROPYRIMIDIN; EFFICIENT METHOD; HIGH YIELD; HOMOGENEOUS; HOMOGENEOUS CATALYST; NON-TOXICITY; SHORT REACTION TIME;

ALDEHYDES; CATALYSTS;

SYNTHESIS (CHEMICAL);

EID: 78549294812     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2010.31.11.3238     Document Type: Article

References (34)

1. Aswal, K. S.; Rovnyak, G. C.; Kinball, S. D.; Floyd, D. M.; Moreland, S.; Swanson, B. N.; Gougoutas, J. Z.; Schwartz, J.; Smillie, K. M.; Mallay, M. F. J. Med. Chem. 1990, 33, 2629.
2. Kappe, C. O.; Fabian, W. M. F.; Semones, M. A. Tetrahedron 1997, 53, 2803.
3. Sinder, B. B.; Shi, Z. J. Org. Chem. 1993, 58, 3828.
4. Kappe, C. O. Acc. Chem. Res. 2000, 33, 879.
5. Kappe, C. O. Tetrahedron 1993, 49, 6937.
6. Kappe, C. O. Eur. J. Med. Chem. 2000, 35, 1043.
7. Jain, K. S.; Bariwal, J. B.; Kathiravan, M. K.; Phoujdar, M. S.; Sahne, R. S.; Chauhan, B. S.; Shah, A. K.; Yadav, M. R. Bioorg. Med. Chem. 2008, 16, 4759.
8. Chiang, A. N.; Valderramos, J.-C.; Balachandran, R.; Chovatiya, R. J.; Mead, B. P.; Schneider, C.; Bell, S. L.; Klein, M. G.; Huryn, D. M.; Chen, X. S.; Day, B. W.; Fidock, D. A.; Wipf, P.; Brodsky, J. L. Bioorg. Med. Chem. 2009, 17, 1527.
9. Patil, A. D.; Kumar, N. V.; Kokke, W. C.; Bean, M. F.; Freyer, A. J.; Brosse, C. D.; Mai, S.; Truneh, S.; Carte, B. J. Org. Chem. 1995, 60, 1182.
10. Biginelli, P. Gazz. Chim. Ital. 1893, 23, 360.
11. Chen, W.; Qin, S. D.; Jin, J. R. Catal. Commun. 2007, 8, 123.
12. Bigdeli, M. A.; Jafari, S.; Mahdavinia, G. H.; Hazarkhani, H. Catal. Commun. 2007, 8, 1641.
13. Khabazzadeh, H.; Saidi, K.; Sheibani, H. Bioorg. Med. Chem. Lett. 2008, 18, 278.
14. Rosi Reddy, K.; Venkateshwar Reddy, C. H.; Mahesh, M.; Raju, P. V. K.; Narayana Reddy, V. V. Tetrahedron Lett. 2003, 44, 8173.
15. Debache, A.; Amimour, M.; Belfaitah, A.; Rhouati, S.; Carboni, B. Tetrahedron Lett. 2008, 49, 6119.
16. Feng Yuan, N. Y. Y.; Cao, Z.; Wang, S. W.; Wang, J. T.; Peppe, C. Teteahedron 2005, 58, 4801.
17. Chitra, S.; Pandiarajan, K. Tetrahedron Lett. 2009, 50, 2222.
18. Bigi, F.; Carloni, S.; Frullanti, B.; Maggi, R.; Sartori, G. Tetrahedron Lett. 1999, 40, 3465.
19. Legeay, J. C.; Eynde, J. J. V.; Bazureau, J. P. Tetrahedron 2008, 64, 5328.
20. Schmidt, R. J.; Lombardo, L. J.; Traeger, S. C.; Williams, D. K. Tetrahedron Lett. 2008, 49, 3009.
21. Polshettiwar, V.; Varma, R. S. Tetrahedron Lett. 2007, 48, 7343.
22. Debache, A.; Amimour, M.; Belfaitah, A.; Rhouati, S.; Carboni, B. Tetrahedron Lett. 2008, 49, 6119.
23. Khabbazzadeh, H.; Saidi, K.; Sheibani, H. Bioorg. Med. Chem. Lett. 2008, 18, 278.
24. Ahmed, N.; Lier, J. E. V. Tetrahedron Lett. 2007, 48, 5407.
25. Cepanec, I.; Litvic, M.; Filipan Litvic, M.; Grüngold, I. Tetrahedron 2007, 63, 11822.
26. Cepanec, I.; Litvic, M.; Bartolincic, M.; Lovric, M. Tetrahedron 2005, 61, 4275.
27. Balalaie, S.; Soleiman-Beigi, M.; Rominger, F. J. Iran Chem. Soc. 2005, 2, 319.
28. Xu, Z.; Zhang, D.; Zou, X. Synth. Commun. 2006, 36, 255.
29. Skibinska, M.; Zahn, F. A.; Czarnocka, A.; Lewenstein, W. Acta Poloniae Pharmaceutica-Drug Res. 1969, 6, 25.
30. Khazaei, A.; Manesh, A. A. J. Chin. Chem. Soc. 2005, 52, 1017.
31. Khazaei, A.; Manesh, A. A. Synthesis 2005, 1929.
32. Semenova, A. A.; Korolov, A. A. Gigiena i Sanitariia 1982, 11.
33. Neuvonen, H.; Neuvonen, K.; Koch, A.; Kleinpeter, E.; Pasanen, P. J. Org. Chem. 2002, 67, 6995.
34. Kappe, C. O. J. Org. Chem. 1997, 62, 7201.