Isolation and structure determination of the first example of the azeto[2,3-c]quinolizinedione ring system

Abstract

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.2015.07.029An 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

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