Synthesis of a bicyclic oxo-gamma-lactam from a simple caprolactam derivative

Weck, Christian and Obst, Franziska and Nauha, Elisa and Schofield, Christopher and Gruber, Tobias (2017) Synthesis of a bicyclic oxo-gamma-lactam from a simple caprolactam derivative. New Journal of Chemistry, 41 . pp. 9984-9989. ISSN 1144-0546

Full content URL: https://doi.org/10.1039/c7nj02348k

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Synthesis of a bicyclic oxo-gamma-lactam from a simple caprolactam derivative
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Item Type:Article
Item Status:Live Archive

Abstract

The synthesis of the 6-azabicyclo[3.2.1]octane ring system, via Dieckmann cyclization, is described. Ring closure involves reaction of a caprolactam enolate with a C-6 ester, the reactive axial conformation of which is promoted by the presence of an N-tert-butyloxycarbonyl group on the lactam nitrogen. The results will enable the synthesis of new bridged caprolactams for testing as antibacterials and nucleophilic enzyme inhibitors.

Keywords:caprolactam, X-ray diffraction, NMR Spectroscopy, Molecular Conformation, drug synthesis
Subjects:F Physical Sciences > F160 Organic Chemistry
F Physical Sciences > F150 Medicinal Chemistry
F Physical Sciences > F151 Pharmaceutical Chemistry
Divisions:College of Science > School of Pharmacy
ID Code:28082
Deposited On:02 Aug 2017 14:24

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