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Chemoselective Synthesis of Polycyclic Spiroindolines and Polysubstituted Pyrroles via the Domino Reaction of 2‑Isocyanoethylindoles

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journal contribution
posted on 19.09.2014, 00:00 by Xiang Wang, Shun-Yi Wang, Shun-Jun Ji
Chemoselective 2-isocyanoethylindole-based domino reactions for the construction of polycyclic spiroindoline derivatives and polysubstituted pyrroles have been developed. The reaction of 2-isocyanoethylindoles and gem-diactivated olefins lead to the polycyclic spiroindoline derivatives (up to 92% yields) in EtOH under reflux conditions. Furthermore, the three-component reaction of 2-isocyanoethylindoles with gem-diactivated olefins and secondary amines afford polysubstituted pyrroles (in moderate yields) in CH3CN under reflux conditions.