Reactions of cephalosporin sulphones 2. Rearrangement of 2α- bromocephem sulphones to pyrroles

Tetrahedron

Volumn 54, Issue 23, 1998, Pages 6565-6570

  Gunda, Tamás E ^a   Szoke, Gabriella N ^a,b  

^a INSTITUTE OF EXPERIMENTAL MEDICINE   (Hungary)

^b UNIVERSITY OF DEBRECEN   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

CEPHALOSPORIN DERIVATIVE; SULFONE DERIVATIVE;

ARTICLE; BROMINATION; CHEMICAL ANALYSIS; CHEMICAL REACTION; DRUG SYNTHESIS; PRIORITY JOURNAL;

EID: 0032482301     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00316-0     Document Type: Article

References (11)

1. 1) First part: Gunda, T. E.; Tamás, L. and Sályi, S. Tetrahedron Lett. 1998, 39, 3061
2. 2) a) Alpegiani, M.; Bissolino, P.; Borghi, D.; Sbraletta, D.; Tonani, R. and Perrone, E. Heterocycles 1993, 36, 1747;
3. b) Alpegiani, M.; Bissolino, P.; Corigli, R.; Del Nero, S.; Perrone, E.; Rizzo, V.; Sacchi, N., Cassinelli, G.; Franceschi, G. J. Med Chem. 1994, 37, 4003
4. 3) Gunda, T. E. and Szoke, G. N. Synth. Commun. 1997, 27, 3395
5. 4) Botta, M.; Crucianelli, M.; Saladino, R. and Nicoletti, R. Heterocycles 1992, 34, 1375
6. 5) Bordwell, F. G. and Jarvis, B. B. J. Org. Chem. 1968, 33, 1182
7. 6) Review article Paquette, L. A.: "The Ramberg-Bäcklund Rearrangement", Org. Reactions 1977, 25, 1
8. 7) a) Cusy, G. and Taylor, J. K. Tetrahedron 1989, 45, 455;
9. b) Kaltemberg, J.; de Waard, E. R. and Huisman, H. O. Tetr. Letters 1973, 1482
10. 8) Jones, R. A.: "Pyrroles and their Benzo-derivatives: Reactivity" in "Comprehensive Heterocyclic Chemistry" (Bird, C. W. and Cheeseman, G. W. H., eds.), vol 4., p 201. Pergamon Press, 1984.
11. 9) The referee suggested an interesting alternative mechanism for the formation of 4: the dibromo derivative A could form via a disproportionation, which, in turn, could hydrolytically cleave to intermediate B. Subsequent cyclisation and elimination results in 4: (Scheme Represented)