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Intramolecular Transamidation of Secondary Amides via Visible-Light-Induced Tandem Reaction
Li Tang1, Xing-Meng Li1, Jack H Matuska2
1Key Laboratory of Applied Chemistry of Chongqing Municipality, School of Chemistry and Chemical Engineering , Southwest University , Chongqing 400715 , China.
Abstract:
Transformation of secondary amides to N-acylimines was used as an effective strategy to activate otherwise unreactive amide bonds. In this tandem reaction, the Rose Bengal-catalyzed photo-oxidative coupling of arylglycine esters and enamides generates N-acylimines, which undergo intramolecular transamidation and imine hydrolysis to afford bioactive acyl Mannich base derivatives under metal-free and mild conditions.
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