Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 14, Pages 6262-6270Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo3011073
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Funding
- National Science Foundation
- National Institutes of Health Center of Excellence for Chemical Methodology and Library Development at the University of Kansas [P50 GM069663]
- National Natural Science Foundation of China [21002021]
- Ministry of Education of China (Scientific Research Foundation for the Returned Overseas Chinese Scholars)
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N-Unsubstituted beta-lactams react with a molecule of aryne by insertion into the amide bond to form a 2,3-dihydroquinolin-4-one, which subsequently reacts with another molecule of aryne to form an acridone by extrusion of a molecule of ethylene. 2,3-Dihydroquinolin-4-ones react under the same reaction conditions to afford identical results. This is the first example of ethylene extrusion in aryne chemistry.
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