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

Kim, Jimin and Stoltz, Brian M. (2012) A C–N insertion of β-lactam to benzyne: unusual formation of acridone. Tetrahedron Letters, 53 (37). pp. 4994-4996. ISSN 0040-4039. doi:10.1016/j.tetlet.2012.07.026. https://resolver.caltech.edu/CaltechAUTHORS:20121029-133109161

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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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1016/j.tetlet.2012.07.026 DOIArticle
http://www.sciencedirect.com/science/article/pii/S0040403912011926PublisherArticle
ORCID:
AuthorORCID
Stoltz, Brian M.0000-0001-9837-1528
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.
Funders:
Funding AgencyGrant Number
AbbottUNSPECIFIED
AmgenUNSPECIFIED
Boehringer IngelheimUNSPECIFIED
Teva USA Scholars ProgramUNSPECIFIED
CaltechUNSPECIFIED
Subject Keywords:beta-Lactam; Benzyne; sigma-Insertion; Ethylene; Acridone
Issue or Number:37
DOI:10.1016/j.tetlet.2012.07.026
Record Number:CaltechAUTHORS:20121029-133109161
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20121029-133109161
Official Citation:Jimin Kim, Brian M. Stoltz, A C–N insertion of β-lactam to benzyne: unusual formation of acridone, Tetrahedron Letters, Volume 53, Issue 37, 12 September 2012, Pages 4994-4996, ISSN 0040-4039, 10.1016/j.tetlet.2012.07.026.
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:35160
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:29 Oct 2012 21:31
Last Modified:09 Nov 2021 23:13

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