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 | ||||||||||||
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| 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. | ||||||||||||
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| 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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