Regiodivergent Synthesis of Penta-Substituted Pyrroles through a Cascade [3 + 2] Cyclization of C‑Acylimines with Activated Alkynes and Aromatic Nucleophiles

Highly robust one-pot, four-component cascade cyclization reaction of α-keto aldehydes, anilines, activated alkynes, and aromatic nucleophiles is developed to synthesize a diverse range of pharmaceutically important penta-substituted pyrroles. The reaction proceeds through the cascade cyclization of acylimines (in situ formed) with activated alkynes and aromatic nucleophiles such as indoles, pyrroles, and naphthols at room temperature under calcium­(II) catalysis with high yields and broad substrate diversity.