1,3-Dibromo 5,5-dimethylhydantoin (DBH): A novel and efficient catalyst for the synthesis of 14-aryl-14H-dibenzo[a, j] xanthenes under solvent-free conditions

Science China Chemistry

Volumn 54, Issue 6, 2011, Pages 957-960

  Forouzani, Mehdi ^a   Ghasemnejad Bosra, Hassan ^b   Habibzadeh, Setareh ^c  

^a University of Payamenoor   (Iran)

^b ISLAMIC AZAD UNIVERSITY   (Iran)

^c Industrial Noshiravani University   (Iran)

Author keywords

DBH; one pot synthesis; solvent free; xanthenes

Indexed keywords

ARYL ALDEHYDES; DBH; ECO-FRIENDLY; EFFICIENT CATALYSTS; ENVIRONMENT FRIENDLY; HIGHER YIELD; MODERATE TEMPERATURE; ONE-POT REACTION; ONE-POT SYNTHESIS; REACTION CONDITIONS; SOLVENT FREE; SOLVENT FREE CONDITIONS; XANTHENES;

ALDEHYDES; CATALYSTS; PHENOLS; SOLVENTS;

SYNTHESIS (CHEMICAL);

EID: 79958202410     PISSN: 16747291     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11426-011-4273-3     Document Type: Article

References (32)

1. J.M. Jamison K. Krabill A. Hatwalkar 1990 Potentiationof the antiviral activityofpoly r(AU) by xanthene dyes Cell Biol Int Rep 14 12 1075 1084 10.1016/0309-1651(90)90015-Q 1:CAS:528:DyaK3MXksVWgtr8%3D
2. A.N.M. El-Brashy M.E. Metwally F.A. El-Sepai 2004 Spectrophotometric determination of some fluoroquinolone antibacterials by binary complex formation with xanthene dyes IL Farmaco 59 10 809 817 10.1016/j.farmac.2004.07.001 1:CAS:528:DC%2BD2cXotlWmsL4%3D (Pubitemid 39335951)
3. K. Chibale M. Visser D.V. Schalkwyk P.J. Smith A. Saravanamuthu A.H. Fairlamb 2003 Exploring the potential of xanthene derivatives as trypanothione reductase inhibitors and chloroquine potentiating agents Tetrahedron 59 13 2289 2296 10.1016/S0040-4020(03)00240-0 1:CAS:528:DC%2BD3sXitFKhtbo%3D (Pubitemid 36331903)
4. R.M. Ion D. Frackowiak 1998 The incorporation of various porphyrins into blood cells measured via flow cytometry, absorption and emission spectroscopy Acta Biochim. Pol 45 3 833 845 1:CAS:528:DyaK1cXntlKkt7Y%3D (Pubitemid 128434271)
5. G. Saint-Ruf H.T. Hieu J.P. Poupelin 1975 The effect of dibenzoxanthenes on the paralyzing action of zoxazolamine Naturwissenschaften 62 12 584 585 10.1007/BF01166986 1:CAS:528:DyaE28XltlOrsQ%3D%3D
6. B.B. Bhowmik P. Ganguly 2005 Photophysics of xanthene dyes in surfactant solution Spectrochim Acta Part A: Mol Biomol Spectr 61 9 1997 2003 10.1016/j.saa.2004.07.031 (Pubitemid 40684119)
7. C.G. Knight T. Stephens 1989 Xanthene-dye-labelled phosphatidylethanolamines as probes of interfacial pH Biochem J 258 683 689 1:CAS:528:DyaL1MXitVyksLo%3D
8. M. Ahmad T.A. King B.H. Cha J. Lee 2002 Performance and photostability of xanthene and pyrromethene laser dyes in sol-gel phases J Phys D Appl Phys 35 13 1473 1476 10.1088/0022-3727/35/13/303 1:CAS:528:DC%2BD38XlsFOitLc%3D (Pubitemid 34789713)
9. R.N. Sen N.J. Sarkar 1925 The condensation of primary alcohols with resorcinol and other hydroxy aromatic compounds J Am Chem Soc 47 4 1079 1091 10.1021/ja01681a023 1:CAS:528:DyaB2MXhtFOhuw%3D%3D
10. A. Jha J. Beal 2004 Convenient synthesis of 12H-benzo[a]xanthenes from 2-tetralone Tetrahedron Lett 45 49 8999 9001 10.1016/j.tetlet.2004.10.046 1:CAS:528:DC%2BD2cXpsVGqt7w%3D (Pubitemid 39504882)
11. C.W. Kuo J.M. Fang 2001 Synthesis of xanthenes, indanes, and tetrahydronaphthalenes via intramolecular phenyl-carbonyl coupling reactions Synth Commun 31 6 877 892 10.1081/SCC-100103323 1:CAS:528:DC%2BD3MXksFGhu70%3D (Pubitemid 32488493)
12. J.Q. Wang R.G. Harvey 2002 Synthesis of polycyclic xanthenes and furans via palladium-catalyzed cyclization of polycyclic aryltriflate esters Tetrahedron 58 29 5927 5931 10.1016/S0040-4020(02)00534-3 1:CAS:528: DC%2BD38XltV2qs74%3D (Pubitemid 34756707)
13. D.W. Knight P.B. Little 1998 The first high-yielding benzyne cyclisation using a phenolic nucleophile: A new route to xanthenes Synlett 10 1141 1143 10.1055/s-1998-1878 (Pubitemid 128723775)
14. R.J. Sarma J.B. Baruah 2005 One step synthesis of dibenzoxanthenes Dyes Pigments 64 1 91 92 10.1016/j.dyepig.2004.03.010 1:CAS:528:DC%2BD2cXmt1WisrY%3D (Pubitemid 39033198)
15. A.R. Khosropour M.M. Khodaei H. Moghannian 2005 A facile, simple and convenient method for the synthesis of 14-alkyl or aryl-14-H-dibenzo [a,j]xanthenes catalyzed by pTSA in solution and solvent-free conditions Synlett 6 955 958 10.1055/s-2005-864837 (Pubitemid 40524265)
16. A. Khoramabadi-zad S.A. Akbari A. Shiri 2005 One-pot synthesis of 14H-dibenzo [a,j)xanthene and its 14-substituted derivatives J Chem Res 5 277 279 10.3184/0308234054323850 (Pubitemid 40910792)
17. B. Rajitha B.S. Kumar Y.T. Reddy P.N. Reddy 2005 Sulfamic acid: A novel and efficient catalyst for the synthesis of aryl-14H-dibenzo[a,j]xanthenes under conventional heating and microwave irradiation Tetrahedron Lett 46 50 8691 8693 10.1016/j.tetlet.2005.10.057 1:CAS:528:DC%2BD2MXhtF2ru7rM (Pubitemid 41617355)
18. B. Das B. Ravikanth R. Ramu K. Laxminarayana B.V. Rao 2006 Sulfamic acid: a novel and efficient catalyst for the synthesis of aryl-14H-dibenzo[a,j] xanthenes under conventional heating and microwave irradiation J Mol Catal A Chem 255 1-2 74 77 10.1016/j.molcata.2006.04.007 1:CAS:528:DC%2BD28XnsFOqtL8%3D (Pubitemid 44067554)
19. A.P. Mohamed P.J. Vaderapura 2007 Molecular iodine catalyzed synthesis of aryl-14H-dibenzo[a,j]xanthenes under solvent-free condition Bioorgan Med Chem Lett 17 3 621 623 10.1016/j.bmcl.2006.11.009 (Pubitemid 46108575)
20. M.A. Mostafa S. Mozhdeh B. Ayoob 2007 Heteropolyacid: An efficient and ecofriendly catalyst for the synthesis of 14-aryl-14H-dibenzo [a,j]xanthene Appl Catal A Gen 323 242 245 10.1016/j.apcata.2007.02.016 (Pubitemid 46528201)
21. M.H. Majid B. Khadijeh D. Zohreh F.B. Fatemeh 2007 Facile heteropolyacidpromoted synthesis of 14-substituted-14-H-dibenzo[a,j]xanthene derivatives under solvent-free conditions J Mol Catal A Chem 273 1 99 101 10.1016/j.molcata.2007.03.041 (Pubitemid 46994765)
22. R.S. Hamid G. Majid H. Asadollah 2008 One-pot synthesis of aryl 14H-dibenzo[a,j]xanthene leuco-dye derivatives Dyes Pigments 76 2 564 568 10.1016/j.dyepig.2006.11.004 (Pubitemid 47382571)
23. S. Mozhdeh M. Peiman B. Ayoob 2008 Solvent-free synthesis of aryl-14H-dibenzo[a,j]xanthenes and 1,8-dioxo-octahydro-xanthenes using silica sulfuric acid as catalyst Dyes Pigments 76 3 836 839 10.1016/j.dyepig.2007.02. 001 (Pubitemid 47412973)
24. S. Ko C.F. Yao 2006 Heterogeneous catalyst: Amberlyst-15 catalyzes the synthesis of 14-substituted-14H-dibenzo[a, j]xanthenes under solvent-free conditions Tetrahedron Lett 47 50 8827 8829 10.1016/j.tetlet.2006.10.072 1:CAS:528:DC%2BD28XhtFyqurfL (Pubitemid 44767856)
25. K. Gong D. Fang H.L. Wanga X.L. Zhou Z.L. Liu 2009 The one-pot synthesis of 14-alkyl- or aryl-14H-dibenzo[a,j]xanthenes catalyzed by task-specific ionic liquid Dyes and Pigments 80 30 33 10.1016/j.dyepig.2008.02.011 1:CAS:528:DC%2BD1cXhtFemt7jF
26. H. Ghasemnejad-Bosra M. Faraje S. Habibzadeh F. Ramzaniyan-Lehmali 2010 An efficient one-pot synthesis of highly substituted furans catalyzed by N-bromosuccinimid J Serb Chem Soc 75 299 305 10.2298/JSC090824025G 1:CAS:528:DC%2BC3cXksVOgsr8%3D
27. D. Azarifar H. Ghasemnejad-Bosra M. A. Zolfigol M. Tajbaksh 2006 Microwave-assisted synthesis of N-arylglycines: improvement of sydnone synthesis Heterocycles 68 175 181 10.3987/COM-05-10574 1:CAS:528:DC%2BD28XhtVyqsbc%3D
28. 2O under neutral conditions: subsequent bromination of these sydnones to their 4-bromo derivatives. Synthesis, 2006, 1123-1126
29. D. Azarifar H. Ghasemnejad-Bosra M. Tajbaksh 2007 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 J Heterocycl Chem 44 467 9 10.1002/jhet.5570440231 1:CAS:528:DC%2BD2sXktFCntLo%3D (Pubitemid 350205252)
30. H. Ghasemnejad-Bosra M. Haghdadi I. Gholampour-Azizi 2008 N-Bromosuccinimide (NBS) as promoter for acylation of sydnones in the presence of acetic anhydride under neutral conditions Heterocycles 75 391 395 10.3987/COM-07-11185 1:CAS:528:DC%2BD1cXit12itrc%3D
31. 2O under neutral conditions J Chin Chem Soc 55 464 467 1:CAS:528:DC%2BD1cXns1ygurw%3D
32. H. Ghasemnejad-Bosra M. Faraje S. Habibzadeh 2009 Efficient one-Pot 1,3-dibromo-5,5-dimethylhydantoin (DBH)-catalyzed synthesis of highly substituted furans Helv Chim Acta 92 575 578 10.1002/hlca.200800310 1:CAS:528:DC%2BD1MXktlSmsLs%3D