1,3-Dibromo-5,5-dimethylhydantoin as a Novel Oxidizing Agent for the Oxidation of 1,3,5-Trisubstituted Pyrazolines under Both Heterogeneous and Solvent-free Conditions

Bulletin of the Korean Chemical Society

Volumn 25, Issue 1, 2004, Pages 23-24

  Azarifar, Davood ^a   Zolfigol, Mohammad Ali ^a   Maleki, Behrooz ^a  

^a BU ALI SINA UNIVERSITY   (Iran)

Author keywords

1,3,5 Trisubstituted pyrazolines; 1,3 Dibromo 5,5 dimethylhydantoin (DBH); Pyrazoles; Solvent free conditions

Indexed keywords

1,3 BROMO 5,5 DIMETHYLHYDANTOIN; AROMATIC COMPOUND; HETEROCYCLIC COMPOUND; HYDANTOIN DERIVATIVE; OXIDIZING AGENT; PYRAZOLE DERIVATIVE; PYRAZOLINE DERIVATIVE; REAGENT; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; OXIDATION; REACTION ANALYSIS; REPRODUCIBILITY; ROOM TEMPERATURE; SYNTHESIS; TECHNIQUE;

EID: 1642421284     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: 10.5012/bkcs.2004.25.1.023     Document Type: Article

References (30)

1. Azarifar, D.; Shaebanzadeh, M. Molecules 2002, 7, 885.
2. Gilchrist, T. L. Heterocyclic Chemistry, 2nd Ed; John Willey & Sons, Inc.: New York, 1992; p 294.
3. Nakamichi, N.; Kawashita, Y.; Hayashi, M. Org. Lett. 2002, 4, 3955.
4. Shah, J. N.; Shah, C. K. J. Org. Chem. 1978, 43, 1266.
5. Goldstone, W. A. F.; Norman, R. O. C. J. Chem. Soc. Chem. Commun. 1966, 1536.
6. Auwers, K.; Heimke, P. Liebigs Ann. 1927, 458, 186.
7. Bhatnagar, I.; George, M. V. Tetrahedron 1968, 24, 1293.
8. Smith, L. I.; Howard, K. L. J. Am. Chem. Soc. 1943, 65, 159.
9. Dodwadmath, R. P.; Wheeler, T. S. Proc. Ind. Acad. Sci. 1935, 2A, 438.
10. Singh, S. P.; Kumar, D.; Prakash, O.; Kapoor, R. P. Synth. Commun. 1997, 27, 2683.
11. Sabitha, G.; Kumar Reddy, G. S. K.; Reddy, Ch. S.; Fatima, N.; Yadav, J. S. Synthesis 2003, 1267.
12. Varma, R. S. Green Chem. 1999, 1, 43.
13. Tanaka, K.; Toda, F. Chem. Rev. 2000, 100, 1025.
14. Krchnak, V.; Holladay, M. W. Chem. Rev. 2002, 102, 61.
15. Hilp, M.; Senjuk, S. J. Pharm. Biomed. Anal. 2001, 25, 363.
16. Hilp, M. Pharmazie 2001, 56, 777.
17. Hilp, M. Pharmazie 2002, 57, 45.
18. Hilp, M. Pharmazie 2002, 57, 316.
19. Hilp, M. J. Pharm. Biomed. Anal. 2002, 28, 303.
20. Hilp, M. J. Pharm. Biomed. Anal. 2002, 28, 337.
21. Walter, T. R.; Zajac, W. W.; Woods, J. M. J. Org. Chem. 1991, 56, 1316.
22. Uchibori, Y.; Umeno, M.; Seto, H.; Yoshioka, I. Chem. Lett. 1993, 4, 673.
23. Shimizu, M.; Nakahara, Y.; Yoshioka, H. J. Chem. Soc. Chem. Commun. 1989, 24, 1881.
24. Sondej, S. C.; Katzenellenbogen, J. A. J. Org. Chem. 1986, 51, 3508.
25. Shimizu, M.; Nakahara, Y.; Yoshioka, H. J. Fluorine Chem. 1999, 97, 57.
26. Chassaing, C.; Haudrechy, A.; Langlois, Y. Tetrahedron Lett. 1997, 38, 4415.
27. Furuta, S.; Hiyama, T. Tetrahedron Lett. 1996, 37, 7983.
28. 1H-NMR,) and physical data with the authentic samples.3-11 All 1,3,5-tri substituted pyrazolines were synthesized according to our previously reported procedure.1
29. 4 (10 mL). The solvent was evaporated and the pyrazoles (2) were obtained (Table). If further purification is needed, flash chromatography on silica gel [eluent: n-hexane: acetone (10:1)] to give highly pure 2.
30. 11 mp 139-140 °C].