Ring Contractionof Bicyclic Lactams: A MolecularEditing Aza-Favorski-Type Approach to Tetrahydroquinoline-2-carboxylicAcids
Abstract
Abstract Development of skeletal editing methods offers new horizons for the acceleration of drug discovery. An original aza-Favorski-type approach is described for the ring contraction of benzazepine-2-ones, providing versatile tetrahydroquinoline-2-carboxylic acids. The sequence employing silylation and Pb(OAc)4-promoted oxidative ring contraction affords variously substituted N-protected derivatives in ≤67% yields. The approach can also be applied to higher homologues, although with a lower efficiency.
// Source
Authors: Viktoria A. Ikonnikova, Kirill D. Kungurtsev, Pavel N. Solyev, Владислав А. Лушпа, Михаил С. Баранов, Dmitry A. Skvortsov, Andrey А. Mikhaylov
Institutions: Pirogov Russian National Research Medical University, Lomonosov Moscow State University, Institute of Bioorganic Chemistry, D. Mendeleyev University of Chemical Technology of Russia, Engelhardt Institute of Molecular Biology