Interesting new rearrangements of the cephalosporin antibiotics

On the course of the preparation of new cephalosporin derivatives with potential HLE inhibiting activity, three new rearrangements were observed. When a 7 beta-aminocephem sulfone (prepared in situ from 2) was diazotized in methanolic HClO4 solution with HNO2, the triazole 3 was prepared in good yie...

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Bibliographic Details
Published inActa pharmaceutica Hungarica Vol. 68; no. 2; p. 79
Main Authors Gunda, T, Gabriella, N S, Tamás, L, Sályi, S
Format Journal Article
LanguageHungarian
Published Hungary 01.03.1998
Subjects
Cephalosporins - chemical synthesis
Cephalosporins - chemistry
Drug Design
Indicators and Reagents
Models, Molecular
Structure-Activity Relationship
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Summary:On the course of the preparation of new cephalosporin derivatives with potential HLE inhibiting activity, three new rearrangements were observed. When a 7 beta-aminocephem sulfone (prepared in situ from 2) was diazotized in methanolic HClO4 solution with HNO2, the triazole 3 was prepared in good yield. On the other hand, the 2 alpha-bromocephem 6 rearranged to two different products, depending on the solvent used. When it was allowed to stay in acetonitrile for 7 days, the bromopyrrol 8 was the product, while in acetone, THF or DMF the aromatic side chain brominated product 7 was obtained. In both cases the inverse polarity of the C-2-Br bond and the easily resulting bromonium ion can be regarded responsible for the rearrangements.
ISSN:0001-6659