We report a highly site-selective direct C5–H and N–H alkylation of free amine group-bearing 8-aminoquinolines in high to excellent yields.

Alkylated imidazopyridines are crucial structures for medicinal chemistry. Here, an efficient method for the C3–H alkylation of imidazopyridines was devised. Under Lewis acid-catalyzed conditions, reactions of imidazopyridines with different donor–acceptor cyclopropanes were carried out. Finally, 1,3-bisfunctionalizaton of donor–acceptor cyclopropanes was performed. In addition, synthesized C3-alkylated imidazopyridines are amenable for diverse synthetic applications.

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