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The first access to <i>N-1</i>, <i>N-4</i> disubstituted pyrrolo[2,3-<i>d</i>][1,2,3]triazoles is reported. The series were generated using a “one-pot” MCR, leading to a single regioisomer of the attempted heteroaromatic skeleton in good yields. Next, the functionalization of <i>C-5</i> and <i>C-6</i> positions was investigated. (Het)aryl groups were introduced at the <i>C-5</i> and <i>C-6</i> positions of the pyrrolo[2,3-<i>d</i>][1,2,3]triazoles using regioselective electrophilic brominations followed by Suzuki–Miyaura cross coupling reactions. Palladium-catalyzed cross-coupling conditions were optimized and a representative library of various boronic acids was employed to establish the scope and limitations of the method.