Eco-friendly and efficient one-pot synthesis of alkyl- or aryl-14H-dibenzo[a,j]xanthenes in water

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 1, 2008, Pages 436-438

  Dabiri, Minoo ^a   Baghbanzadeh, Mostafa ^a   Nikcheh, Maryam Shakouri ^a   Arzroomchilar, Elham ^a  

^a SHAHID BEHESHTI UNIVERSITY   (Iran)

Author keywords

Aldehyde; Green chemistry; Heterocycle; Water; Xanthene

Indexed keywords

2 NAPHTHOL; ALDEHYDE DERIVATIVE; ALKYL GROUP; ALUMINUM POTASSIUM SULFATE; BENZENE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SOLVENT; WATER; XANTHENE DERIVATIVE;

ACIDITY; AQUEOUS SOLUTION; ARTICLE; CATALYST; ONE POT SYNTHESIS; QUANTUM YIELD; REACTION ANALYSIS; REACTION TIME;

ALDEHYDES; ALUM COMPOUNDS; CHEMISTRY, ORGANIC; NAPHTHOLS; SOLVENTS; WATER; XANTHENES;

EID: 37649004405     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.07.008     Document Type: Article

References (35)

1. Hideo, T. Chem. Abstr. 1981, 95, 80922b, Jpn. Tokkyo Koho JP 56005480, 1981.
2. Lambert, R. W.; Martin, J. A.; Merrett, J. H.; Parker, K. E. B.; Thomas, G. J. PCT Int. Appl. WO9706178, 1997.
3. Poupelin J.P., Ruf G.S., Blanpin O.F., Narcisse G., Ernouf G.U., and Lacroix R. Eur. J. Med. Chem. 13 (1978) 67
4. Ion R.M., Planner A., Wiktorowicz K., and Frackowiak D. Acta Biochim. Pol. 45 (1998) 833
5. Menchen, S. M.; Benson, S. C.; Lam, J. Y. L.; Zhen, W.; Sun, D.; Rosenblum, B. B.; Khan, S. H.; Taing, M. US Patent 6583168, 2003.
6. Banerjee A., and Mukherjee A.K. Stain Technol. 56 (1981) 83
7. Bekaert A., Andrieux J., and Plat M. Tetrahedron Lett. 33 (1992) 2805
8. Buehler C.A., Cooper D.E., and Scrudder E.O. J. Org. Chem. 8 (1943) 316
9. Licudine P.J.A., Kawate M.K., and Li Q.X. J. Agric. Food Chem. 45 (1997) 766
10. Papini P., and Cimmarusti R. Gazz. Chim. Ital. 77 (1947) 142
11. Sen R.N., and Sarkar N. J. Am. Chem. Soc. 47 (1925) 1079
12. Ota K., and Kito T. Bull. Chem. Soc. Jpn. 49 (1976) 1167
13. Ko S., and Yao C.-F. Tetrahedron Lett. 47 (2006) 8827
14. Rajitha B., Kumar B.S., Reddy Y.T., Reddy P.N., and Sreenivasulu N. Tetrahedron Lett. 46 (2005) 8691
15. Das B., Ravikanth B., Ramu R., Laxminarayana K., and Rao B.V. J. Mol. Catal. A: Chem. 255 (2006) 74
16. Pasha M.A., and Jayashankara V.P. Bioorag. Med. Chem. Lett. 17 (2007) 621
17. Sarma R.J., and Baruah J.B. Dyes Pigm. 64 (2005) 91
18. Khosropour A.R., Khodaei M.M., and Moghannian H. Synlett (2005) 955
19. Grieco P.A. Organic Synthesis in Water (1998), Blackie Academic and Professional, London
20. Demko Z.P., and Sharpless K.B. J. Org. Chem. 66 (2001) 7945
21. Li C.-J. Chem. Rev. 105 (2005) 3095
22. Narayan S., Muldoon J., Finn M.G., Fokin V.V., Kolb H.C., and Sharpless K.B. Angew. Chem., Int. Ed. 44 (2005) 3275
23. Salehi P., Dabiri M., Zolfigol M.A., and Baghbanzadeh M. Tetrahdron Lett. 46 (2005) 7051
24. Dabiri M., Salehi P., Mohammadi A.A., and Baghbanzadeh M. Synth. Commun. 35 (2005) 279
25. Dabiri M., Salehi P., Mohammadi A.A., Baghbanzadeh M., and Kozehgiry G. J. Chem. Res., (S) (2004) 570
26. Salehi P., Dabiri M., Zolfigol M.A., and Baghbanzadeh M. Synlett (2005) 1155
27. Salehi P., Dabiri M., Baghbanzadeh M., and Bahramnejad M. Synth. Commun. 36 (2006) 2287
28. Salehi P., Dabiri M., Zolfigol M.A., and Baghbanzadeh M. Heterocycles 62 (2005) 1417
29. Dabiri M., Salehi P., Zolfigol M.A., and Baghbanzadeh M. Heterocycles 71 (2007) 677
30. Dabiri M., Salehi P., Baghbanzadeh M., Zolfigol M.A., and Bahramnejad M. Synth. Commun. 37 (2007) 1201
31. Dabiri M., Salehi P., Baghbanzadeh M., Vakilzadeh Y., and Kiani S. Monatsh. Chem. 138 (2007) 595
32. Dabiri M., Salehi P., Otokesh S., Baghbanzadeh M., Kozehgary Gh., and Mohammadi A.A. Tetrahedron Lett. 46 (2005) 6123
33. Baghbanzadeh M., Salehi P., Dabiri M., and Kozehgary Gh. Synthesis (2006) 344
34. Salehi P., Dabiri M., Zolfigol M.A., Otokesh S., and Baghbanzadeh M. Tetrahedron Lett. 47 (2006) 2557
35. General procedure for the synthesis of alkyl- or aryl-14H-dibenzo[a,j]xanthenes: A mixture of β-naphthol (2 mmol), aldehyde (1 mmol) and alum (0.5 mmol) in water (3 mL) was heated at 100 °C with stirring for appropriate time (see Table 2). After completion of the reaction confirmed by TLC (eluent: n-hexane/ethylacetate 2:1), mixture was cooled to room temperature and the precipitated product was filtered and recrystallized from ethanol.