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Published on: June 20, 2014
Photoinduced Minisci-type reaction for selective C-H bond carbamoylation of acridines without external oxidant
Yurong Duan1, Xudong Xia2, Yanru Mao1
1Shaanxi Key Laboratory of Chemical Reaction Engineering, College of Chemistry and Chemical Engineering, Yan'an University, Yan'an, Shaanxi, 716000, China. zhaoyyau@163.com.
Abstract:
Herein, a photoinduced Minisci-type reaction for selective C-H bond carbamoylation of acridines without external oxidant and photocatalyst is described. In this reaction, 4-substituted 1,4-dihydropyridines act as radical precursors, and PhCO2H and K2CO3 facilitate the activation of acridines and dehydroaromatization. This method exhibits a good functional group tolerance and broad substrate scopes for direct synthesis of 9-carbamoyl- and acyl-substituted acridine derivatives in good to excellent yields under mild reaction conditions. Its synthetic application is demonstrated by a late-stage installation of acridine into amino acids and active pharmaceutical molecules.
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