DOI QR코드

DOI QR Code

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

  • Published : 2004.01.20

Abstract

Keywords

References

  1. Azarifar, D.; Shaebanzadeh, M. Molecules 2002, 7, 885. https://doi.org/10.3390/71200885
  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. https://doi.org/10.1021/ol0268135
  4. Shah, J. N.; Shah, C. K. J. Org. Chem. 1978, 43, 1266. https://doi.org/10.1021/jo00400a060
  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. https://doi.org/10.1002/jlac.19274580112
  7. Bhatnagar, I.; George, M. V. Tetrahedron 1968, 24, 1293. https://doi.org/10.1016/0040-4020(68)88080-9
  8. Smith, L. I.; Howard, K. L. J. Am. Chem. Soc. 1943, 65, 159. https://doi.org/10.1021/ja01242a008
  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. https://doi.org/10.1080/00397919708004136
  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. https://doi.org/10.1039/a808223e
  13. Tanaka, K.; Toda, F. Chem. Rev. 2000, 100, 1025. https://doi.org/10.1021/cr940089p
  14. Krchnak, V.; Holladay, M. W. Chem. Rev. 2002, 102, 61. https://doi.org/10.1021/cr010123h
  15. Hilp, M.; Senjuk, S. J. Pharm. Biomed. Anal. 2001, 25, 363. https://doi.org/10.1016/S0731-7085(00)00505-7
  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. https://doi.org/10.1016/S0731-7085(01)00589-1
  20. Hilp, M. J. Pharm. Biomed. Anal. 2002, 28, 337. https://doi.org/10.1016/S0731-7085(01)00618-5
  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. https://doi.org/10.1021/jo00368a022
  25. Shimizu, M.; Nakahara, Y.; Yoshioka, H. J. Fluorine Chem. 1999,97, 57. https://doi.org/10.1016/S0022-1139(99)00026-3
  26. Chassaing, C.; Haudrechy, A.; Langlois, Y. Tetrahedron Lett.1997, 38, 4415. https://doi.org/10.1016/S0040-4039(97)00943-X
  27. Furuta, S.; Hiyama, T. Tetrahedron Lett. 1996, 37, 7983. https://doi.org/10.1016/0040-4039(96)01788-1

Cited by

  1. O, as a Novel and Convenient Oxidizing Agent vol.35, pp.19, 2005, https://doi.org/10.1080/00397910500214136
  2. Microwave-assisted Aromatization of 1,3,5-Trisubstituted 2-Pyrazolines by Silica-supported N-Bromosuccinimide as a Useful Reagent under Solvent Free ‘Dry’ Condition vol.65, pp.4, 2005, https://doi.org/10.3987/COM-04-10276
  3. from Hydrogen Peroxide/Acids/Iodide Potassium or Sodium Systems vol.32, pp.12, 2011, https://doi.org/10.5012/bkcs.2011.32.12.4366
  4. 1,3,5-Trichloro-2,4,6-Triazinetrion: A Versatile Heterocycle for the One-Pot Synthesis of 14-Aryl- or Alkyl -14H-Dibenzo[a,j]xanthene, 1,8-Dioxooctahydroxanthene and 12-Aryl-8,9,10,12-Tetrahydrobenzo[a]xanthene-11-one Derivatives under Solvent-Free Conditions vol.32, pp.5, 2011, https://doi.org/10.5012/bkcs.2011.32.5.1697
  5. Tricholoroisocyanuric Acid as a Useful Reagent in Microwave-assisted Aromatization of 1,3,5-Trisubstituted 2-Pyrazolines vol.52, pp.6, 2013, https://doi.org/10.1002/jccs.200500174
  6. Mild and efficient oxidation of 2-pyrazolines and isoxazolines by trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxalane–NH4Cl–HOAc in water–MeCN vol.41, pp.8, 2015, https://doi.org/10.1007/s11164-014-1626-5
  7. Use of Bromine and Bromo-Organic Compounds in Organic Synthesis vol.116, pp.12, 2016, https://doi.org/10.1021/acs.chemrev.5b00400
  8. 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. vol.35, pp.32, 2004, https://doi.org/10.1002/chin.200432139
  9. Microwave-promoted Aromatization of 1,3,5-trisubstituted 4,5-Dihydro-1H-pyrazoles by Calcium Hypochlorite under Solvent-free Conditions vol.68, pp.6, 2006, https://doi.org/10.3987/COM-06-10701
  10. Oxidative Aromatization of 3,5-Disubstituted Isoxazolines to the Corresponding Isoxazoles with N,N,N’,N’-Tetrabromobenzene-1,3-disolfonamide (TBBDS) and 1,3-Dibromo-5,5-dimetylhydantoin (DBH) as Efficient Reagents under Mild Reaction Conditions vol.71, pp.3, 2007, https://doi.org/10.3987/COM-06-10961
  11. Silica Sulfuric Acid-Activated Poly-1,3,- dichloro-5-methyl-5-(4’-vinylphenyl)hydantoin (PDCVH) as an Effective Reagent for Oxidation of 1,3,5-Trisubstituted 2-Pyrazolines Both under Microwave Irradiation and Thermal Conditions vol.75, pp.3, 2008, https://doi.org/10.3987/COM-07-11248
  12. 1,3-Dibromo-5,5-dimethylhydantoin (DBH) as an efficient promoter for acetylation of 3-arylsydnones in the presence of acetic anhydride under neutral conditions vol.44, pp.2, 2007, https://doi.org/10.1002/jhet.5570440231
  13. respectively from sodium nitrite and sodium nitrate in acetic acid vol.45, pp.2, 2008, https://doi.org/10.1002/jhet.5570450241
  14. 1,3-Dibromo-5,5-diethylbarbituric acid as an efficient catalyst for the protection of various alcohols with HMDS under solvent-free conditions vol.8, pp.6, 2004, https://doi.org/10.1016/j.catcom.2006.07.012
  15. The first report on the catalytic oxidation of urazoles to their corresponding triazolinediones via in situ catalytic generation of Br+ using periodic acid or oxone®/KBr syst vol.270, pp.1, 2004, https://doi.org/10.1016/j.molcata.2007.02.003
  16. Oxidative Aromatization of 1,3,5-Trisubstituted 4,5-Dihydro-1H-Pyrazoles Efficiently by Tetrabromine-1,3,5,7-Tetrazatricyclo[3.3.1.13,7]Decane Complex, Br4-Tatcd, as a Novel Reag vol.56, pp.1, 2004, https://doi.org/10.1002/jccs.200900007
  17. Silica-supported 1,3-dichloro-5,5-dimethylhydantoin (DCH) as a useful reagent for microwave-assisted aromatization of 1,3,5-trisubstituted pyrazolines under solvent-free conditions vol.22, pp.4, 2004, https://doi.org/10.1016/j.cclet.2010.10.023
  18. Environmentally friendly procedure for the aqueous oxidation of benzyl alcohols to aldehydes with dibromodimethylhydantoin (DBDMH) and cyclodextrin: Scope and mechanistic insights vol.46, pp.7, 2004, https://doi.org/10.1080/00397911.2016.1161801
  19. Oxidative Aromatization of 1,3,5-trisubstituted 2-pyrazolines Using Oxalic Acid/Sodium Nitrite System vol.39, pp.2, 2004, https://doi.org/10.1080/10406638.2016.1267019
  20. Thermal electron-transfer-induced oxidation of 2-pyrazolines vol.23, pp.4, 2004, https://doi.org/10.1007/s11030-019-09922-x
  21. Pd(0)‐guanidine@MCM‐41: a very effective catalyst for rapid production of bis (pyrazolyl)methanes vol.34, pp.6, 2004, https://doi.org/10.1002/aoc.5579