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

Fernandez-Diaz-Ropero, Beatriz; Elsegood, Mark; Fairley, Gary; Pritchard, Gareth; Teat, Simon J.; Weaver, George

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

journal contribution

posted on 2015-09-11, 10:51 authored by Beatriz Fernandez-Diaz-Ropero, Mark ElsegoodMark Elsegood, Gary Fairley, Gareth PritchardGareth Pritchard, Simon J. Teat, George WeaverGeorge Weaver

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.

Funding

The authors thank AstraZeneca and Loughborough University for providing funding.

History

School

Science

Department

Chemistry

Published in

Tetrahedron Letters

Citation

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.

Publisher

Version

AM (Accepted Manuscript)

Publisher statement

This work is made available according to the conditions of the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0) licence. Full details of this licence are available at: https://creativecommons.org/licenses/by-nc-nd/4.0/

Publication date

2015

Notes

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