Chemodivergent Approach to 1,2,3-Triazole-Fused Quinazolines

We have developed a convenient approach to the assembly of 1,2,3-triazole-fused quinazolines through the cyclization of 5-iodotriazoles bearing a pendant sulfonamide moiety. The C(sp2)–N bond formation proceeds efficiently as a base-promoted halogen substitution in the triazole ring. The rational choice of base and solvent enables the chemodivergent synthesis of either triazole-fused quinazolines or their dihydro derivatives. The potential applications of the target heterocycles were illustrated by their involvement in Rh-catalyzed denitrogenative amidation.