A novel and efficient solvent-free and heterogeneous method for the synthesis of primary, secondary and bis-N-acylsulfonamides using metal hydrogen sulfate catalysts

Tetrahedron

Volumn 65, Issue 36, 2009, Pages 7696-7705

  Massah, Ahmad Reza ^a   Asadi, Beheshteh ^a   Hoseinpour, Mahdieh ^a   Molseghi, Azadeh ^a   Kalbasi, Roozbeh Javad ^a   Javaherian Naghash, Hamid ^a  

^a ISLAMIC AZAD UNIVERSITY   (Iran)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; METAL DERIVATIVE; SULFATE; SULFONAMIDE;

ACYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL;

EID: 67949103779     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.06.112     Document Type: Article

References (39)

1. Banwell M.G., Crasto C.F., Easton C.J., Forrest A.K., Karoli T., March D.R., Mensah L., Nairn M.R., O'Hanlon P.J., Oldham M.D., and Yue W. Bioorg. Med. Chem. Lett. 10 (2000) 2263
2. Chang L.L., Ashton W.T., Flanagan K.L., Chen T.B., O'Malley S.S., Zingaro G.J., Siegl P.K.S., Kivlighn S.D., Lotti V.J., Chang R.S.L., and Greenless W.J. J. Med. Chem. 37 (1994) 4464
3. Singh S.K., Vobbalareddy S., Kalleda S.R., Casturi S.R., Mullangi R., Ramanujam R., Yeleshwarapu K.R., and Iqbal J. Bioorg. Med. Chem. Lett. 16 (2006) 3921
4. Huang S., Connolly P.J., Lin R., Emanuel S., and Middleton S.A. Bioorg. Med. Chem. Lett. 16 (2006) 3639
5. Allegretti M., Bertini R., Cesta M.C., Bizzarri C., Bitondo R.D., Cioccio V.D., Galliera E., Berdini V., Topai A., Zampella G., Russo V., Bello N.D., Nano G., Nicolini L., Locati M., Fantucci P., Florio S., and Colotta F. J. Med. Chem. 48 (2005) 4312
6. Chambers M.S., Hobbs S.C., Graham M.I., Watt A.P., Fletcher S.R., Baker R., Freedman S.B., Patel S., Smith A.J., and Matassa V.G. Bioorg. Med. Chem. Lett. 5 (1995) 2303
7. Schaaf T.K., and Hess H.J. J. Med. Chem. 22 (1979) 1340
8. Yee Y.K., Bernstein P.R., Adams E.J., Brown F.J., Cronk L.A., Hebbel K.C., Vacek E.P., Krell R.D., and Synder D.W. J. Med. Chem. 33 (1990) 2437
9. Guzzo P.R., Teng M., and Miller M.J. Tetrahedron 50 (1994) 8275
10. Pelletier J.C., and Hesson P.D. Synlett (1995) 1141
11. Johnson D.C., and Widlanski T.S. Tetrahedron Lett. 42 (2001) 3677
12. Kondo K., Sekimoto E., Nakao J., and Murakami Y. Tetrahedron 56 (2000) 5843
13. Wang Y., Soper D., Dirr M.J., deLong M.A., De B., and Wos J.A. Chem. Pharm. Bull. 48 (2000) 1332
14. Ishizuka N., Matsumura K.I., Hayashi K., Sakai K., and Yamamori T. Synthesis (2000) 6784
15. Ishizuka, N.; Matsumura, K.I. Japanese Patent JP-10045705, 1998.
16. Morisawa Y., Kataoka M., Negahori H., Sakamoto T., Kitano N., and Kusano K. J. Med. Chem. 23 (1980) 1376
17. Martin M.T., Roschangar F., and Eaddy J.F. Tetrahedron Lett. 44 (2003) 5461
18. Toda F., and Tanaka K. Chem. Rev. 100 (2000) 1025
19. Massah A.R., Mosharafian M., Momeni A.R., Aliyan H., Javaherian Nagash H., and Adibnejad M. Synth. Commun. 37 (2007) 1807
20. Kazemi F., Massah A.R., and Javaherian H. Tetrahedron 63 (2007) 5083
21. Chai F., Cao F., Zhai F., Chen Y., Wang X., and Su Z. Adv. Synth. Catal. 349 (2007) 1141
22. Massah A.R., Momeni A.R., Dabagh M., Aliyan H., and Javaherian Nagash H. Synth. Commun. 38 (2007) 265
23. Shaterian H.R., Yarahmadi H., and Ghashang M. Tetrahedron 64 (2008) 1263
24. Salehi P., Zolfigol M.A., Shirini F., and Baghbanzadeh M. Curr. Org. Chem. 10 (2006) 2171
25. Shirini F., Zolfigol M.A., Salehi P., and Abedini M. Curr. Org. Chem. 12 (2008) 182
26. Shirini F., Zolfigol M.A., Safari A., Mohammadpoor-Baltork I., and Mirjalili B.F. Tetrahedron Lett. 44 (2003) 7463
27. Zolfigol M.A., Bagherzadeh M., Mallakpour S.E., Chehardoli G., Kolvari E., Ghorbani Choghamarani A., and Koukabi N. Catal. Commun. 8 (2007) 256
28. Mirjalili B.F., Zolfigol M.A., Bamoniri A., Karimi-Zarchi M.A., Zaghaghi Z., and Parvaideh M. J. Iran. Chem. Soc. 4 (2007) 340
29. Massah A.R., Kazemi F., Azadi D., Farzaneh S., Aliyan H., Javaherian Nagash H., and Momeni A.R. Lett. Org. Chem. 3 (2006) 235
30. Massah A.R., Dabagh M., Afshar M., Momeni A.R., Aliyan H., and Javaherian Naghash H. Turk. J. Chem. 31 (2007) 611
31. Massah A.R., Azadi D., Aliyan H., Javaherian Nagash H., Momeni A.R., and Kazemi F. Monatsh. Chem. 139 (2008) 233
32. Barthos R., Lonyi F., Engelhardt J., and Valyon J. Top. Catal. 10 (2000) 79
33. Hughes T.R., and Whites H.M. J. Phys. Chem. 69 (1965) 2192
34. Datka J., Turek A.M., Jehng J.M., and Wachs I.E. J. Catal. 135 (1992) 186
35. Parry E.R. J. Catal. 2 (1963) 371
36. Flego C., Kiricsi I., Perego C., and Bellussi G. Stud. Surf. Sci. Catal. 99 (1995) 2110
37. Emeis C.A. J. Catal. 141 (1993) 347
38. Hubert O.C., and Louis H. J. Chem. Soc., Chem. Commun. (1937) 1114
39. Frederick K. J. Chem. Soc., Chem. Commun. (1949) 3029