Facile kinetic induction of a dihydropyridide to pyrrolide ring contraction

David R. Carbery, Michael S. Hill, Mary F. Mahon, Catherine Weetman

OAI: oai:purehost.bath.ac.uk:openaire_cris_publications/9bfbcd58-a8dc-4a86-8ea9-cc7ebe1f1349 • DOI: https://doi.org/10.1039/C5DT02887F

Reactions between magnesium 1,4-dihydropyridide or 1,2-dihydro-iso-quinolide derivatives and carbodiimides, RN=C=NR, generally result in Mg-N insertion and formation of guanidinate complexes. More sterically perturbed systems with N-aryl carbodiimide substitution, however, follow a divergent course of reaction initiating heterocyclic ring contraction and pyrrolide formation under unprecedentedly mild conditions.