A facile
approach to a range of substituted 7-(benzimidazol-2-yl)thioxolumazines
[7-(benzimidazol-2-yl)-2-thioxo-2,3-dihydropteridin-4(1H)-ones] and 7-(benzimidazol-2-yl)lumazines [7-(benzimidazol-2-yl)pteridine-2,4(1H,3H)-diones] is described. These new biheterocyclic
systems are obtained via H2SO4-catalyzed rearrangement
of quinoxalin-2-ones in the presence of 5,6-diamino-2-mercapto- and
2,5,6-triaminopyrimidin-4-ols. Thus, benzimidazole and pteridine rings
are constructed in one synthetic step. A plausible ANRORC (addition of nucleophile, ring opening and ring closure)-type reaction mechanism is proposed. Applying the rearrangement
to the aza-analogue of 3-benzoylquinoxalin-2(1H)-onei.e.,
3-benzoylpyrido[2,3-b]pyrazin-2(1H)-onewith 5,6-diamino-2-mercaptopyrimidin-4-ol makes it possible
to synthesize inaccessible 7-(1H-imidazo[4,5-b]pyridin-2-yl)-6-phenyl-2-thioxo-2,3-dihydropteridin-4(1H)-one. 7-(Benzimidazol-2-yl)-6-(2-fluorophenyl)-2-thioxo-2,3-dihydropteridin-4(1H)-ones undergoes intramolecular nucleophilic substitution
of fluorine by a nitrogen of the benzimidazole fragment with the formation
of benzo[4′,5′]imidazo[1′,2′:1,2]quinolino[4,3-g]pteridine-2,4(1H,3H)-diones
as new heterocyclic systems.
The reaction of 3-benzoylquinoxalin-2(1H)-ones with enamines (generated in situ from ammonium acetate and the corresponding methylaryl(hetaryl)ketones) proceeds smoothly to give the corresponding substituted 1-(pyrrolyl)benzimidazolone derivatives in moderate yields through the novel rearrangement of 3-benzoylquinoxalin-2(1H)-ones involving a dual cleavage of the C3═N4 and C2-C3 bonds under mild conditions.
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