Artyukhova Y. Behavior of dialkylaminonaphthalic acid derivatives under conditions of the Vilsmeier—Haack reaction

The objects – dialkylaminonaphthalic, dimethylaminothionaphthalic acid derivatives and related compounds; the goal – to clear up the direction of the reaction of dialkylaminonaphthalic acid derivatives towards the Vilsmeier—Haack complex (POCl3—DMF) and to apply these reactions to synthesise organic dyes and luminophores; the methods – organic synthesis, X-ray analysis, mass-spectrometry, 1H-NMR, IR, molecular absorption and fluorescence spectroscopy, quantum chemical semi-empirical simulations of molecular structure and spectral properties; the novelty – we are first who has investigated behaviour of systematic series of dialkylaminonaphthalic acid derivatives, 4-dimethylaminothionaphthalic acid derivatives and related compounds under conditions of the Vilsmeier—Haackreaction. Using quantum chemical simulations the mechanism of quinazolinium salts formation under substitution with the Vilsmeier—Haack reagent ortho to tert.-amino group has been first investigated. The structures of products of 1,2,3,4-tetrahydroquinazolin-3-ium salts alkali hydrolysis have been first determined. Influence of formation and cleavage of 1,2,3,4-tetrahydroquinazolin-3-ium ring on the spectral and luminescent properties have been studied. A systematic series of monothio- and dithio-naphthalic methyl and phenylimides has been first synthesised, biophysical investigation of quenching of fluorescence of series of model biological objects has been implemented; degree of application - synthetic procedure for 3-formyl-4-dimethylaminonbenzoic acid has been patented in Ukraine. Two patent on fluorescent staining of polymeric materials using the tetrahydroquinazolinium salts have been applied. Several luminophores have been used as fluorescent biomedical labels at LJL Biosystems company (USA). The new methods for biomedical testing with use of the synthesised fluorescence quenchers, thionaphthalic acid derivatives, are currently in development in the Institute for Scintillation Materials of the NAS of Ukraine