Several 3-styryl derivatives of 1,4-benzodiazine-2-one and of 1-methyl-1,4-benzodiazine-2-one were prepared. A structural study of these compounds by 1H and 13C NMR and by molecular modelling was carried out. The rotational isomerism around the bond connecting the imine and vinyl groups in these E styrylbenzodiazinones is discussed. The s-cis rotamer is shown to be the predominant isomer. The photophysical properties of these fluorescent dyes are reported.
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.
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