Optimized conditions for copper-catalyzed N-arylation of methyl pyroglutamate are described. These studies permitted the synthesis of methyl N-naphthylpyroglutamate, which was then cyclized to a ketone. The known dehydration of amidoketones by PPA was extended to this new scaffold to lead to a novel condensed benzo [de] quinoline with potential antioxidative activity.
[Trusova, Marina E.; Krasnokutskaya, Elena A.; Postnikov, Pavel S.; Choi, Younghwa; Chi, Ki-Whan; Filimonov, Victor D. Synthesis, 2011 , # 13 p. 2154 - 2158]