ChemInform Abstract: Unusual [3 + 2] Cycloaddition of Acrylic Acid Derivatives to 7‐Formyl‐4,5,6,7‐tetrahydro‐4,5,7‐trimethylpyrrolo[3,2‐c]pyridine under Michael Reaction Conditions.

Abstract

Unusual [3 + 2] Cycloaddition of Acrylic Acid Derivatives to 5,6,5,pyridine under Michael Reaction Conditions.-Reaction of 2formyltetrahydropyrrolopyridine (I) with acrylic acid derivatives (II) in the presence of Trilon B r does not afford the common Michael adducts but proceeds via [3 + 2] cycloaddition to furnish the pyridopyrrolizines (III) as mixture of diastereomers. Similar reaction of acrylonitrile (IV) does not stop at the formation of analogous 8-cyano-substituted adduct but affords isomeric 8-cyano-8-cyanoethyl derivatives (V) and (VI) resulting from a further cyanoethylation. -(VARLAMOV, A. V.; BORISOVA, T. N.; BARGE, S. B.; VOSKRESENSKY, L. G.; CHERNYSHEV, A. I.; SEMENOVA, E. M.; Khim.