Styrylbenzodiazinones 2. Chromo- et fluoroionophores dérivés du monoaza-15-couronne-5. Synthèse et structure

Abstract

In connection with our work on styryl derivatives of benzodiazinones, we have prepared the 7-N,N-dimethylamino-3-methyl-1,4-benzodiazin-2-one 4a and two chromo- and fluoroionophores derived from the monoaza-15-crown-5 and styrylbenzodiazinones. A structural study of these compounds by 1H and 13C NMR, UV spectrophotometry, and molecular modelling was carried out. Unlike styrylbenzoxazinones, styrylbenzodiazinone derivatives showed a Z/E isomerization in acetonitrile solution. The isomerization was photoinduced, was catalysed by metallic ions, and was a reversible process. As well, an efficient alkylation reaction of the lactam function of benzodiazinones is described.