1,3-Dibromo-5,5-dimethylhydantoin as a useful reagent for efficient synthesis of 3,4-dihydropyrimidin-2-(1H)-ones under solvent-free conditions

Chemical Papers

Volumn 63, Issue 1, 2009, Pages 97-101

  Abdollahi Alibeik, Mohammad ^a   Zaghaghi, Zahra ^a  

^a YAZD UNIVERSITY   (Iran)

Author keywords

1,3 dibromo 5,5 dimethylhydantoin; 3,4 dihydropyrimidin 2 (1H) one; Microwave irradiation; Solvent free synthesis

Indexed keywords

EID: 56749102785     PISSN: 03666352     EISSN: 13369075     Source Type: Journal    
DOI: 10.2478/s11696-008-0084-1     Document Type: Article

References (34)

1. K. S. Atwal B. N. Swanson S. E. Unger D. M. Floyd S. Moreland A. O. Hedberg B. C. O'Reilly 1991 Dihydropyrimidine calcium channel blockers. 3. 3-Carbamoyl-4-aryl-1,2,3,4-tetrahydro-6-methyl-5-pyrimidinecarboxylic acid esters as orally effective antihypertensive agents Journal of Medicinal Chemistry 34 806 811
2. J. Auerbach S. A. Weissman T. J. Blacklock M. R. Angeles L. Hoogsteen 1993 N-bromosuccinimide/dibromodimethylhydantoin in aqueous base: a practical method for the bromination of activated benzoic acids Tetrahedron Letters 34 931 934
3. D. Azarifar M. A. Zolfigol B. Maleki 2004 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 25 23 24
4. D. Azarifar B. Maleki K. Mohammadi 2007 Oxidative aromatization of 3,5-disubstituted isoxazolines to the corresponding isoxazoles with N, N, N', N'-tetrabromobenzen-1,3-disolfonamide (TBBDS) and 1,3-dibromo-5,5- dimethylhydantoin (DBH) as efficient reagents under mild reaction conditions Heterocycles 71 683 689
5. J. Barluenga M. Tomas A. Ballesteros L. A. Lopez 1989 1,4-Cycloaddition of 1,3-diazabutadienes with enamines: An efficient route to the pyrimidine ring Tetrahedron Letters 30 4573 4576
6. P. Biginelli 1893 Aldehyde-urea derivatives of aceto-and oxaloacetic acids Gazzetta Chimica Italiana 23 360 413
7. J. C. Bussolari P. A. McDonnell 2000 A new substrate for the Biginelli cyclocondensation: direct preparation of 5-unsubstituted 3,4-dihydropyrimidin- 2(1H)-ones from a β-keto carboxylic acid Journal of Organic Chemistry 65 6777 6779
8. C. Chassaing A. Hauderchy Y. Langlois 1997 1,3-Dibromo-5,5- dimethylhydantoin, a useful reagent for aromatic bromination Tetrahedron Letters 38 4415 4416
9. 5 amides and esters Tetrahedron 62 4651 4664
10. H. Eguchi H. Kawaguchi S. Yoshinnaga A. Nishida T. Nishiguchi S. Fujisaki 1994 Halogenation using N-halogenocompounds. II. Acid catalyzed bromination of aromatic compounds with 1,3-dibromo-5,5-dimethylhydantoin Bulletin of the Chemical Society of Japan 67 1918 1921
11. 3-catalysed one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones Journal of Molecular Catalysis A: Chemical 217 47 50
12. Gohain, M., Prajapati, D., & Sandhu, J. S. (2004). A novel Cu-catalysed three-component one-pot synthesis of dihydropyrimidin-2(1H)-ones using microwaves under solvent-free conditions. Synlett, 235-238. DOI: 10.1055/s-2003-43374.
13. Hazarkhani, H., & Karimi, B. (2004). N-Bromosuccinimide as an almost neutral catalyst for efficient synthesis of dihydropyrimidinones under microwave irradiation. Synthesis, 1239-1242. DOI: 10.1055/s-2004-822348.
14. M. Hilp 2002 Determination of selenium sulfide using 1,3-dibromo-5,5- dimethylhydantoin (DBH) Analytical methods of pharmacopeias with DBH in respect to environmental and economical concern part 11 Journal of Pharmaceutical and Biomedical Analysis 28 337 343
15. E. H. Hu D. R. Sidler U. H. Dolling 1998 Unprecedented catalytic three component one-pot condensation reaction: an efficient synthesis of 5-alkoxycarbonyl-4-aryl-3,4-dihydropyrimidin-2(1H)-ones Journal of Organic Chemistry 63 3454 3457
16. C. O. Kappe 1993 100 Years of the Biginelli dihydropyrimidine synthesis Tetrahedron 49 6937 6963
17. C. O. Kappe W. M. F. Fabian M. A. Semones 1997 Conformational analysis of 4-aryl-dihydropyrimidine calcium channel modulators. A comparison of ab initio, semiempirical and X-ray crystallographic studies Tetrahedron 53 2803 2816
18. H. Khabazzadeh K. Saidi H. Sheibani 2008 Microwave-assisted synthesis of dihydropyrimidin-2(1H)-ones using graphite supported lanthanum chloride as a mild and efficient catalyst Bioorganic & Medicinal Chemistry Letters 18 278 280
19. Khazaei, A., Zolfigol, M. A., & Rostami, A. (2004). 1,3-Dibromo-5,5-dimethylhydantoin [DBDMH] as an efficient and selective agent for the oxidation of thiols to disulfides in solution or under solvent-free conditions. Synthesis, 2959-2961. DOI: 10.1055/s-2004-834919.
20. 2O-mediated three-component, one-pot, condensation reaction: an efficient synthesis of 4-arylsubstituted 3,4-dihydropyrimidin-2-ones Tetrahedron Letters 42 7873 7875
21. Lu, J., & Ma, H. R. (2000). Iron (III)-catalyzed synthesis of dihydropyrimidinones. Improved conditions for the biginelli reaction. Synlett, 63-64. DOI: 10.1055/s-2000-6469.
22. L. E. Overman M. H. Rabinowitz P. A. Renhowe 1995 Enantioselective total synthesis of (-)-ptilomycalin A Journal of the American Chemical Society 117 2657 2658
23. A. D. Patil N. V. Kumar W. C. Kokke M. F. Bean A. J. Freyer C. De Brosse S. Mai A. Truneh D. J. Faulkner B. Carte A. L. Breen R. P. Hertzberg R. K. Johnson J. W. Westly B. C. M. Potts 1995 Novel alkaloids from the Sponge Batzella SP.: Inhibitors of HIV gp120-Human CD4 binding Journal of Organic Chemistry 60 1182 1188
24. Ramalinga, K., Vijayalakshmi, P., & Kaimal, T. N. B. (2001). Bismuth(III)-catalyzed synthesis of dihydropyrimidinones: improved protocol conditions for the Biginelli reaction. Synlett, 863-865. DOI: 10.1055/s-2001-14587.
25. B. C. Ranu A. Hajra U. Jana 2000 Indium(III) chloride-catalyzed one-pot synthesis of dihydropyrimidinones by a three component coupling of 1,3-dicarbonyl compounds, aldehydes and urea: an improved procedure for the Biginelli reaction Journal of Organic Chemistry 65 6270 6272
26. I. Saxena D. C. Borah J. C. Sarma 2005 Three component condensations catalyzed by iodine-alumina the synthesis of substituted 3,4-dihydropyrimidin- 2(1H)-ones under microwave irradiation and solvent-free conditions Tetrahedron Letters 46 1159 1160
27. A. Shaabani A. Maleki 2007 Three-component, one-pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones catalyzed by bromodimethylsulfonium bromide Chemical Papers 61 333 336
28. Shirini, F., Zolfigol, M. A., & Paktinat, M. (2006). Efficient trimethylsilylation and tetrahydropyranylation of alcohols in the presence of 1,3-dibromo-5,5-dimethylhydantoin. Synthesis, 4252-4256. DOI: 10.1055/s-2006-950350.
29. B. B. Snider J. Chen A. D. Patil A. J. Freyer 1996 Synthesis of the tricyclic portions of batzelladines A, B and D. Revision of the stereochemistry of batzelladines A and D Tetrahedron Letters 37 6977 6980
30. Tu, S., Fang, F., Zhu, S., Li, T., Zhang, X., & Zhuang, Q. (2004). A new Biginelli reaction procedure using potassium hydrogen sulfate as the promoter for an efficient synthesis of 3,4-dihydropyrimidin-2(1H)-one. Synlett, 537-539. DOI: 10.1055/s-2004-815419.
31. Varala, R., Alam, M. M., & Adapa, S. R. (2003). Bismuth triflate catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones: An improved protocol for the Biginelli reaction. Synlett, 67-70. DOI: 10.1055/s-2003-36216.
32. 5-catalyzed rapid and efficient synthesis of 3,4-dihydropyrimidinones under ambient conditions Chemistry Letters 33 926 927
33. Y. Yu D. Liu C. Liu G. Luo 2007 One-pot synthesis of 3,4- dihydropyrimidin-2(1H)-ones using chloroacetic acid as catalyst Bioorganic & Medicinal Chemistry Letters 17 3508 3510
34. Zolfigol, M. A., Nasr-Isfahani, N., Mallakpour, S., & Safaiee, M. (2005). Oxidation of urazoles with 1,3-dihalo-5,5-dimethylhydantoin, both in solution and under solvent-free conditions. Synlett, 761-764. DOI: 10.1055/s-2005-863706.