Cephalosporin free radical compounds

Details Cephalosporin free radical compounds Cephalosporin free radical compounds

1990-03-28

1991-08-06

Rizzo, Nicholas S.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

540221, 540222, 540226, 540227, 540215, 540228, C07D50114

Patent

active

050379755

ABSTRACT:
The invention provides a free radical process for preparing 1-carba(1-dethia)cephalosporin antibiotics with 2-substituted methylcephalosporin 1,1-dioxides wherein the substituent on the 2-methylene group is a free radical precursor group such as a phenyl or alkylseleno group. The latter dioxides are treated with a free radical initiator, e.g., a trialkyltin hydride or actinic radiation at 40.degree. C. to 150.degree. C. to provide the 1-carba-3-cephem and 1-carba-2-cephem products. The invention also provides free radical compounds formed as intermediates in the process.

REFERENCES:
patent: 3660395 (1972-05-01), Wright
patent: 3660396 (1972-05-01), Wright
Kametani, T. et al., "Synthesis of Carbacepham and Carbacephem Ring Systems by Employing Radical Cyclization", Heterocycles, vol. 27, No. 4, 1988.
Kametani, T. et al., "Formation of Carbacephem Ring System by 1,6-Bond Coupling Through a Radical Cyclization Reaction", Heterocycles, vol. 19, No. 10, 1982.

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