UV-Spectral and Quantum Chemical Studies of Deoxyvasicinone and Its Derivatives

Comparison of the spectral parameters and results of quantum chemical calculations showed that electrondonating substituents in the 6-position of deoxyvasicinone (DOV) direct electrophilic substitution reactions to the 5- and 7-positions, have no influence on the polarization of the C=O bond, and decrease the reactivity (RA) toward reduction of the N1=C2 bond and substitution of the C9 H atom. Protonation of N1 and introduction of a nitro group in the 6-position of DOV changes the direction of the RA of these centers.