2-BROMO- AND 2-NITROXY DERIVATIVES OF 3-BROMO- AND 3.3-DIBROMO-4-OXO-AZETIDINES, PROCESSES FOR THE PREPARATION THEREOF AND USE THEREOF

摘要

The invention relates to novel 2-bromo- and 2-nitroxy derivatives of3-bromo- and 3,3-dibromo-4-oxo-azetidines, to processes for the preparationthereof and to theuse thereof wherein the novel compounds have the formula:(see foemula I)¦wherein R1 and R2 are hydrogen or bromine, R3 is Me2-C=C-COOR4 wherein R4 ishydrogen, methyl, benzyl or some other carboxy-protective group, and X isbromineor nitroxy group (-ONO2). 2-bromo- and 2-nitroxy derivatives of 3-bromo- and3,3-dibromo-4-oxo-azetidines are prepared by reacting derivatives of protectedpenicillanic acid 1,1-dioxides with DBN reactant and treated with thionylchloride, theobtained residue is passed through a silica gel column with methylene chlorideaseluant or the obtained residue is dissolved in tetrahydrofuran and treatedwithtetrabutyl ammonium bromide and after the treatment a derivative of 2-bromo,3-bromo or 2-bromo-3,3-dibromo-4-oxo-azetidine is isolated, which derivativemay besubjected to a reaction with silver nitrate in 2-propanol and, after thetreatment of thereaction mixture, derivatives of 2-nitroxy-, 3-bromo-or 2-nitroxy-3,3-dibromo-4-oxo-azetidine are isolated. The obtained substances are useful intermediates inthesynthesis of beta lactam analogons or as components in formulations havingantibacterial, inhibitory, antitumour or antagonistic action.