Thiolative Annulation of N-Benzyl-N-cyanopropiolamides Leading to Divergent Synthesis of Pyrroloquinazolin-1-ones and Maleimides

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An unprecedented successive radical-promoted thiolative annulation/Pd-catalyzed C–H amination of N -benzyl- N -cyanopropiolamides to access pyrrolo[2,1- b ]quinazolin-1(9 H )-ones in a one-pot manner is described. Moreover, altering the amination step with oxidation (reagent switch) offered maleimides from the same set of readily accessible precursors. Both transformations display versatility across a wide range of substrates, enabling the efficient access to various functionalized quinazolin-1-ones and maleimides in good yields.