Formation of Acridones by Ethylene Extrusion in the Reaction of Arynes with β-Lactams and Dihydroquinolinones

Y Fang, DC Rogness, RC Larock…

Index: Fang, Yuesi; Rogness, Donald C.; Larock, Richard C.; Shi, Feng Journal of Organic Chemistry, 2012 , vol. 77, # 14 p. 6262 - 6270

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Citation Number: 27

Abstract

N-Unsubstituted β-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.