α-C–H/N–H Annulation of Alicyclic Amines via Transient Imines: Preparation of Polycyclic Lactams
- Weijie ChenWeijie ChenCenter for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611, United StatesMore by Weijie Chen
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- Daniel Seidel*Daniel Seidel*Email: [email protected]Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611, United StatesMore by Daniel Seidel
Abstract
Polycyclic lactams are prepared in a single operation from o-toluamides and cyclic amines in a process that involves transient cyclic imines, species that are conveniently obtained in situ from the corresponding lithium amides and simple ketone oxidants. Imines thus generated, such as 1-pyrroline and 1-piperideine, engage lithiated o-toluamides in a facile annulation process. Undesired side reactions such as imine deprotonation and o-toluamide dimerization are suppressed through the judicious choice of reaction conditions.
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