Synthesis of tetrahydrobenzazepinesulfonamides and their rearrangement to diarylsulfones

Synthetic Communications

Volumn 36, Issue 3, 2006, Pages 355-363

  Ren, Hui ^a   Zanger, Murray ^a   McKee, James R ^a  

^a UNIVERSITY OF THE SCIENCES   (United States)

Author keywords

Acid catalyzed rearrangements; Benzazepine; Sulfonamides; Sulfones

Indexed keywords

1 (2 NITROPHENYLSULFONYL) 2,3,4,5 TETRAHYDRO 1H 1 BENZAZEPINE; 1 BENZENESULFONYL 2,3,4,5 TETRAHYDRO 1H 1 BENZAZEPINE; 7 (2 NITROPHENYLSULFONYL) 2,3,4,5 TETRAHYDRO 1H 1 BENZAZEPINE; 7 CHLORO 1 (2 NITROPHENYLSULFONYL) 2,3,4,5 TETRAHYDRO 1H 1 BENZAZEPINE; 7 CHLORO 1 (PHENYLSULFONYL) 2,3,4,5 TETRAHYDRO 1H 1 BENZAZEPINE; 7 CHLORO 9 (2 NITROPHENYLSULFONYL) 2,3,4,5 TETRAHYDRO 1H 1 BENZAZEPINE; 7 CHLORO 9 (PHENYLSULFONYL) 2,3,4,5 TETRAHYDRO 1H 1 BENZAZEPINE; 9 (2 NITROPHENYLSULFONYL) 2,3,4,5 TETRAHYDRO 1H 1 BENZAZEPINE; 9 (PHENYLSULFONYL) 2,3,4,5 TETRAHYDRO 1H 1 BENZAZEPINE; BENZAZEPINE DERIVATIVE; SULFONAMIDE; SULFONE DERIVATIVE; TETRAHYDROBENZAZEPINE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; DRUG SYNTHESIS; HUMAN IMMUNODEFICIENCY VIRUS; ISOMER; REACTION ANALYSIS; SUBSTITUTION REACTION;

EID: 31544455874     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910500377495     Document Type: Article

References (13)

1. Gennaro, A.; Zanger, M. J. Org. Chem. 1971, 36, 375.
2. (a) Witt, O. N.; Uermenyi, D. Ber. 1913, 46, 296;
3. (b) Witt, O. N.; Truttwin, H. Ber. 1914, 47, 2786.
4. (a) Halberkamm, J. Ber. 1921, 54, 1665, 1833;
5. (b) Halberkamm, J. Ber. 1922, 55, 3074.
6. McMahon, J. M.; Gulakowski, R. J.; Weislow, O. S.; Schultz, R. J.; Narayanan, V. L.; Clanton, D. J.; Pedemonate, R.; Wassmundt, F. W.; Buckheit, R. W.; Decker, J. W. D.; White, E. L.; Bader, J. P.; Boyd, M. R. Antimicrob. Agents Chemother. 1993, 37, 754.
7. Buckheit, R. W., Jr.; Fliakas-Boltz, V.; Russell, J. D.; Snow, M.; Pallansch, L. A.; Yang, S. S.; Dader, J. P.; Khan, T. N.; Zanger, M. Antiviral Chem. Chemother. 1996, 7, 243.
8. Newman, M. S.; Hung, W. M. J. Org. Chem. 1973, 38, 4073.
9. Horning, E. C.; Stromberg, V. L.; Lloyd, A. H. J. Am. Chem. Soc. 1952, 74, 5153.
10. Albrecht, H.; Duber, E. O. Tetrahedron 1984, 40, 1157.
11. Braun, J. V.; Bartsch, B. Ber. 1912, 45, 3384.
12. Yamada, K.; Kubo, T.; Tokuyama, H.; Fukuyama, T. Synlett 2001, 2, 231.
13. Chen, W.; Cilman, N. W. J. Heterocycl. Chem. 1983, 20, 663.