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J Org Chem. 2013 Sep 20;78(18):9424-30. doi: 10.1021/jo401652k. Epub 2013 Sep 11.

The synthesis of benzo[f]isoindole-1,3-dicarboxylates via an i2-induced 1,3-dipolar cycloaddition reaction.

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  • 1State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology , Hangzhou 310032, P. R. China.


An I2-induced 1,3-dipolar cycloaddition reaction has been developed for the synthesis of benzo[f]isoindole-1,3-dicarboxylates from quinones and N-substituted amino esters. The reaction proceeds in good to excellent yields in one step from 3 equiv of amino ester to react with the quinone structure. The utility of this transformation has been highlighted by its use for the construction of benzo[f]isoindole-1,3-dicarboxylates, which have been identified in natural products exhibiting important biological activities.

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