Isolation and structure determination of the first example of the azeto[2, 3-c]quinolizinedione ring system. Issue 36 (2nd September 2015)

• Record Type: Journal Article
• Authors: Fernandez, Beatriz; Elsegood, Mark R.J.; Fairley, Gary; Pritchard, Gareth J.; Teat, Simon J.; Weaver, George W.
• Is Part Of: Tetrahedron letters. Volume 56:Issue 36(2015)
• Page Start: 5120
• Page End: 5122
• Publication Date: 2015-09-02
• Subjects: β-Lactam -- Quinolizinone -- Pyridone -- Drug scaffolds; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.07.029
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: An unexpected azeto[2, 3- c ]quinolizinedione has been isolated during synthetic studies on the base catalyzed condensation of ethyl 6-methylpyridin-2(1 H )-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.