STYRYLBENZODIAZINONES .2. CHROMOIONOPHORE S AND FLUOROIONOPHORES DERIVED FROM 15-MONOAZA-5-CROWN - SYNTHESIS AND STRUCTURE

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