Ylidic polyfunctionalized compounds with a diazinium skeleton

Abstract

For the first time in the cycloimmonium ylide series we have obtained unsaturated styryl carbanion monosubstituted ylides. These ylides, phthalazinium- and 4-methylpyrimidinium- ylides, have polyfunctionalized character: ylide and alkene. In this paper we have exploited only the ylidic character. The ylides 3 and 4 have been proven to have 1,3-dipole characters (3a and 4a), respectively. Thus, the ylides function as 1,3-dipoles in 3+2 dipolar cycloaddition reactions with various dipolarophiles (such as DMAD, NPM). The structure of all the other compounds (salts and cycloadducts) has been proven through elemental and spectral (IR, NMR) analysis. The in vitro biological activity of the newly obtained phthalazine and pyrimidine compounds was also tested. Some of them have proved to have a remarkable activity against different microorganisms (germs and fungus). Correlation of the structure-biological activity has been studied.