N-acylation of sulfonamides using N-acylbenzotriazoles

Arkivoc

Volumn 2004, Issue 12, 2004, Pages 14-22

  Katritzky, Alan R ^a   Hoffmann, Sebastian ^a   Suzuki, Kazuyuki ^a  

^a University of Florida ^*  (United States)

Author keywords

N Acylation; N Acylbenzotriazole; N Acylsulfonamide; Sulfonamides

Indexed keywords

BENZENE DERIVATIVE; BENZYL N [1 BENZYL 2 [[(4 METHYLPHENYL)SULFONYL]AMINO] 2 OXOETHYL]CARBAMATE; BENZYL N [1 METHYL 2 [(METHYLSULFONYL)AMINO] 2 OXOETHYL]CARBAMATE; BENZYL N [1 METHYL 2 [[(4 METHYLPHENYL)SULFONYL]AMINO] 2 OXOETHYL]CARBAMATE; BENZYL N [2 [[[5 (ACETYLAMINO) 1,3,4 THIADIAZOL 2 YL]SULFONYL]AMINO] 1 METHYL 2 OXOETHYL]CARBAMATE; CHLORINE DERIVATIVE; N (1H PYRROL 2 YLCARBONYL) 4 METHYLBENZENESULFONAMIDE; N (1H PYRROL 2 YLCARBONYL)METHANESULFONAMIDE; N (2 FURYLCARBONYL) 4 METHYLBENZENESULFONAMIDE; N (3A,7A DIHYDRO 1H INDOL 2 YLCARBONYL) 4 METHYLBENZENESULFONAMIDE; N (4 METHOXYBENZOYL) 4 METHYLBENZENESULFONAMIDE; N (4 METHOXYBENZOYL) 4 METHYLSULFONAMIDE; N (4 METHYLBENZOYL) 4 METHYLBENZENESULFONAMIDE; N (4 METHYLBENZOYL)METHANESULFONAMIDE; N 4 DIMETHYL N (4 METHYLBENZOYL)BENZENESULFONAMIDE; N [4 (DIETHYLAMINO)BENZOYL] 4 METHYLBENZENESULFONAMIDE; N [5 [(ISONICOTINOYLAMINO)SULFONYL] 1,3,4 THIADIAZOL 2 YL]ACETAMIDE; N [5 [[(4 METHYLBENZOYL)AMINO]SULFONYL] 1,3,4 THIADIAZOL 2 YL]ACETAMIDE; N [5 [[(4 NITROBENZOYL)AMINO]SULFONYL] 1,3,4 THIADIAZOL 2 YL]ACETAMIDE; N ISONICOTINOYL 4 METHYLBENZENESULFONAMIDE; N ISONICOTINOYLMETHANESULFONAMIDE; SODIUM DERIVATIVE; SULFONAMIDE; SULFONE DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; REACTION ANALYSIS;

EID: 5044232912     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (33)

1. (a) Hasegawa, T.; Yamamoto, H. Bull. Chem. Soc. Jpn. 2000, 73, 423.
2. (b) 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.; Yue, W. Bioorg. Med. Chem. Lett. 2000, 10, 2263.
3. (c) Wang, Y.; Soper, D. L.; Dirr, M. J.; deLong, M. A.; De, B.; Wos, J. A. Chem. Pharm. Bull. 2000, 48, 1332.
4. (d) 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.; Greenlee, W. J. J. Med. Chem. 1994, 37, 4464.
5. (e) Musser, J. H.; Kreft, A. F.; Bender, R. H. W.; Kubrak, D. M.; Grimes, D.; Carlson, R. P.; Hand, J. M.; Chang, J. J. Med. Chem. 1990, 33, 240.
6. (a) Kondo, K.; Sekimoto, E.; Nakao, J., and Murakami, Y. Tetrahedron 2000, 56, 5843.
7. (b) Kondo, K.; Sekimoto, E.; Miki, K., and Murakami, Y. J. Chem. Soc. Perkin Trans. 1 1998, 2973.
8. (c) Ishizuka, N.; Matsumura, K.; Hayashi, K.; Sakai, K.; Yamamori, T. Synthesis 2000, 6, 784.
9. (d) Ishizuka, N.; Matsumura, K. Jpn. Kokai Tokkyo Koho JP 10045705; Chem. Abstr. 1998, 128,140463.
10. (e) Inoe, T.; Myahara, O.; Takahashi, A.; Nakamura, Y. Jpn. Kokai Tokkyo Koho JP 08198840; Chem. Abstr. 1996, 125, 247385.
11. (a) Berry, D. J.; Digiovanna, C. V.; Metrick, S. S.; Murugan, R. Arkivoc 2001(i), 201.
12. (b) Yijima, C.; Hino, F., and Suda, K. Synthesis 1981, 610.
13. Martin, M. T.; Roschangar, F.; Eaddy, J. F. Tetrahedron Lett. 2003, 44, 5461.
14. (a) Katritzky, A. R.; He, H.-Y.; Suzuki, K. J. Org. Chem. 2000, 65, 8210.
15. (b) Katritzky, A. R.; Yang, H.; Zhang, S.; Wang, M. Arkivoc 2002(xi), 39.
16. (c) Katritzky, A. R.; Yang, B.; Semenzin, D. J. Org. Chem. 1997, 62, 726.
17. (d) Katritzky, A. R.; Wang, M.; Yang, H.; Zhang, S.; Akhmedov, N. G. Arkivoc 2002(viii), 134.
18. (e) Katritzky, A. R.; Suzuki, K.; Singh, S. K., synthesis, accepted.
19. (f) Katritzky, A. R.; Wang, M.; Zhang, S. Arkivoc 2001(ix), 19.
20. (a) Katritzky, A. R., and Pastor, A. J. Org. Chem. 2000, 65, 3679.
21. (b) Katritzky, A. R.; Abdel-Fattah, A. A. A.; Wang, M. J. Org. Chem. 2003, 68, 4932.
22. (c) Katritzky, A. R.; Abdel-Fattah, A. A. A.; Wang, M. J. Org. Chem. 2003, 68, 1443.
23. (d) Katritzky, A. R.; Suzuki, K.; Singh, S. K.; He, H.-Y. J. Org. Chem. 2003, 68, 5720.
24. (e) Katritzky, A. R.; Suzuki, K.; Singh, S. K. Croat. Chem. Acta 2004, 77, 175.
25. (a) Katritzky, A. R.; Pastor, A.; Voronkov, M. V. J. Heterocyclic Chem. 1999, 36, 777.
26. (b) Katritzky, A. R.; Denisko, O. V.; Fang, Y.; Zhang, L.; Wang, Z. Arkivoc 2001(xi), 41.
27. Katritzky, A. R.; Zhang, Y.; Singh, S. K. Synthesis 2003, 2795.
28. Arnswald, M.; Neumann, W. P., J. Org. Chem. 1993, 58, 7022.
29. Dolyuk, V. G.; Kremlev, M. M.; Rovinskii, M. S. Voprosy Khimii Khimicheskoi Tekhnologii, 34, 11; Chem. Abstr. 1974, 83, 28026.
30. Dolyuk, V. G.; Kremlev, M. M.; Rovinskii, M. S. Voprosy Khimii Khimicheskoi Tekhnologii, 34, 11; Chem. Abstr. 1974, 83, 28026.
31. Papadopoulos, E. P. J. Org. Chem. 1972, 37, 351.
32. Drummond, J. T.; Johnson, G. Tetrahedron Lett. 1988, 29, 1653.
33. Wieland, T.; Hennig, H. J. Chem. Ber. 1960, 93, 1236.