FERNANDEZ, B. ...et al., 2015. Isolation and structure determination of the first example of the azeto[2,3-c]quinolizinedione ring system. Tetrahedron Letters, 56(36), pp.5120-5122.
An unexpected azeto[2,3-c]quinolizinedione has been isolated during synthetic studies on the base catalyzed condensation of ethyl 6-methylpyridin-2(1H)-on-1-ylacetate with benzil. Closure of a fused four-membered azetidinone ring occurred when potassium hexamethyldisilazide was employed as the base. The structure of the product was confirmed by synchrotron X-ray crystallography. A possible mechanism for the formation of the product is considered.
This paper was accepted for publication in the journal Tetrahedron Letters and the definitive published version is available at http://dx.doi.org/10.1016/j.tetlet.2015.07.029
The authors thank AstraZeneca and Loughborough University for providing funding.