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The reaction of tert-butyl 2-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-ylamino) ethylcarbamate with CF3COOH/CH2Cl2 yields 5-chloro-3,4-dihydrobenzo[f]quinoxalin6(2H)-one which undergoes acid-promoted dehydrogenation in the presence of water to give novel 5-chlorobenzo[f]quinoxalin-6-ol. The molecular structure of 5-chlorobenzo[f]quinoxalin6-ol in the solid state, determined by an X-ray diffraction (XRD) study, and the solution data confirm that it exists as the enol-imine tautomer, both in the solid state and in solution, differently from 5-chloro-3,4-dihydrobenzo[f]quinoxalin-6(2H)-one, which exhibits the keto-amine arrangement. Density functional theory (DFT) calculations confirmed the preference of 5-chlorobenzo[f]quinoxalin-6-ol and of the derivatives containing H and CH3 groups in place of the Cl atom for the enol-imine tautomer. It is suggested that the enol-imine structure is preferred for 5-chlorobenzo[f]quinoxalin-6-ol as a consequence of the higher aromatic character of this structure in comparison with the keto-amine form. DFT calculations carried out on the two tautomers of the benzo[a]phenazin-5(7H)-ones analogous to the benzo[f]quinoxalin-6(4H)-ones showed that the relative stabilities are dominated by solvation effects in the first case and the degree of aromaticity, in the latter.

journal of the brazilian chemical society

Tautomerism in Quinoxalines Derived from the 1,4-Naphthoquinone Nucleus: Acid Mediated Synthesis, X-ray Molecular Structure of 5-Chlorobenzo[<i>f</i>]quinoxalin-6-ol and Density Functional Theory Calculations

Tautomerism in Quinoxalines Derived from the 1,4-Naphthoquinone Nucleus: Acid Mediated Synthesis, X-ray Molecular Structure of 5-Chlorobenzo[f]quinoxalin-6-ol and Density Functional Theory Calculations