Abstract

Ph3P-I2-mediated condensation reactions of isatoic anhydrides and o-phenylenediamines have been developed for the regioselective syntheses of a wide range of linearly and angularly fused benzoimidazoquinazolinones. The selectivity of the products relies on the generation of either highly electrophilic oxyphosphonium or less reactive imidate intermediates. A direct amine attack at the C-2 position of the oxyphosphonium intermediate presumably drives the reaction toward the linearly fused products, whereas an attack of the diamine at the C-4 position of the in situ generated cyclic imidate leads to the angularly fused derivatives. This strategy serves as a practical handle for the efficient synthesis of other related heterocycles.

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