Welcome to the new version of CaltechAUTHORS. Login is currently restricted to library staff. If you notice any issues, please email coda@library.caltech.edu
Published September 12, 2012 | public
Journal Article

A C–N insertion of β-lactam to benzyne: unusual formation of acridone


Intermolecular insertion of benzyne into the C–N bond of a β-lactam is described. This σ-insertion is followed by ring expansion that produces dihydroquinolinone, which rapidly reacts with an additional benzyne unit to afford an acridone through intramolecular C–C bond formation to the carbonyl group and rapid elimination of ethylene.

Additional Information

© 2012 Elsevier Ltd. Received 29 June 2012. Revised 4 July 2012. Accepted 6 July 2012. Available online 16 July 2012. The authors acknowledge Abbott, Amgen, Boehringer Ingelheim, the Teva USA Scholars Program, and Caltech for financial support. We also thank Dr. Pamela Tadross and Mr. Christopher Haley for helpful discussions and materials.

Additional details

August 22, 2023
October 20, 2023