TY - JOUR
T1 - Transformations of penicillins
T2 - New methods of formation and reactions of 6,6-disubstituted penams and 7,7-disubstituted cephems
AU - Bremner, David H
AU - Campbell, Malcolm M
AU - Johnson, Graham
PY - 1976
Y1 - 1976
N2 - The reactions of penicillanate esters with ethyl or trichloroethyl N-chloro-N-sodiocarbamate gave 6a-ethoxyformamido and 6a- trichloroethoxyformamido-6ß-acylaminopenicillanates, respectively. The 6a-trichloroethoxyformamido-group was transformed in certain penicillanates into a 6a-amino-group. 7ß-Acylamino-7a- ethoxyformamidodeacetoxycephalosporanates were formed from the appropriate 6,6-disubstituted penicillanate S-oxides. The reaction of the 6,6-disubstituted penicillanates with phosgene led to a 1-ethoxycarbonyl-2-oxo-3-phenoxyacetyl-1, 3-diazetidine-4-spiro-6'-penicillanate.
AB - The reactions of penicillanate esters with ethyl or trichloroethyl N-chloro-N-sodiocarbamate gave 6a-ethoxyformamido and 6a- trichloroethoxyformamido-6ß-acylaminopenicillanates, respectively. The 6a-trichloroethoxyformamido-group was transformed in certain penicillanates into a 6a-amino-group. 7ß-Acylamino-7a- ethoxyformamidodeacetoxycephalosporanates were formed from the appropriate 6,6-disubstituted penicillanate S-oxides. The reaction of the 6,6-disubstituted penicillanates with phosgene led to a 1-ethoxycarbonyl-2-oxo-3-phenoxyacetyl-1, 3-diazetidine-4-spiro-6'-penicillanate.
UR - http://www.scopus.com/inward/record.url?scp=0016905502&partnerID=8YFLogxK
M3 - Article
SN - 1472-7781
VL - 18
SP - 1918
EP - 1924
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
ER -