Synthesis of Medium Ring Nitrogen Heterocycles via a Tandem Copper-Catalyzed C−N Bond Formation−Ring-Expansion Process
- 1 March 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 126 (11), 3529-3533
- https://doi.org/10.1021/ja038565t
Abstract
A simple method for the preparation of medium ring heterocycles (7-, 8-, 9-, and 10-membered) has been developed. The process employs a Cu-catalyzed coupling of a β-lactam with an aryl bromide or iodide followed by intramolecular attack of a pendant amino group. In some instances, the intermediate β-lactam is observable but can be converted to the aza-heterocycle by catalysis. Acetic acid was found to be superior to transition metal complexes as a catalyst for this ring-expansion process.Keywords
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