CaltechAUTHORS
Published September 12, 2012 | Version Campus-Access Only
Journal Article Metadata-only

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

Creators

Abstract

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.

External Files

Files attached to this record are restricted to users connected to the Caltech campus network:

Additional details

Identifiers

Eprint ID
35160
Resolver ID
CaltechAUTHORS:20121029-133109161

Funding

Abbott
Amgen
Boehringer Ingelheim
Teva USA Scholars Program
Caltech

Dates

Created
2012-10-29
Created from EPrint's datestamp field
Updated
2021-11-09
Created from EPrint's last_modified field