Copper-Catalyzed and 1,3-Sulfonyl Migration Enabled Installation of Azaindoles in the Periphery of Aryl Rings: Synthesis of Sulfonylated Pyrrolo[2,3-]quinolines and Investigation of Antimalarial Potency.

Herein, an atom efficient and one-pot protocol, offering a series of sulfonylated pyrrolo[2,3-]quinolines via C-N, C-C, and C-S bond formation, has been developed with an inexpensive copper catalyst. Notably, the reaction proceeds via a double-annulation reaction followed by a 1,3-sulfonyl migration sequence. Moreover, the method is applicable to a broad range of 2-carbonylanilines. Furthermore, synthetic applications and the scale-up reaction highlight the utility potential of this protocol. In addition, the antimalarial property of sulfonylated pyrrolo[2,3-]quinolines showed parasite inhibition without cytotoxic effects in mammalian cells.