Divergent Approach for Regioselective Synthesis of Linearly and Angularly Fused Benzoimidazoquinazolinones from Isatoic Anhydrides.

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.

Citation

Mookda Pattarawarapan, Dolnapa Yamano, Surat Hongsibsong, Wong Phakhodee. Divergent Approach for Regioselective Synthesis of Linearly and Angularly Fused Benzoimidazoquinazolinones from Isatoic Anhydrides. The Journal of organic chemistry. 2022 Dec 02;87(23):16063-16073

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PMID: 36372967

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