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The molecular structure and absorption spectra of monothio- and dithio-naphthalimides were compared to their naphthalimide analogues using AM1, PM3 and ZINDO/S semiempirical quantum chemical methods. The substitution of the 4R-naphthalimide oxygen atoms by sulphur atoms resulted in a red-shift of the absorption spectra by Δλ max 60-65 and 100-140 nm, respectively. The thionated naphthalimide...
The quaternized 1,3-diazine ring formation qualified as a particular case of the t-amino effect has been found under conditions of the Vilsmeier-Haack formylation of 4-dialkylaminonaphthalic acid derivatives. The diazinium ring is hydrolyzed in alkaline media with dealkylation, and 3-dimethylamino-4-alkylamino derivatives are formed.
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