Copper-Catalyzed Cyanoisopropylalkenylation of N-Alkenyl-acrylamides to Give 1,3-Dihydropyrrol-2-ones

Abstract

A copper-catalyzed cyanoisopropylation/cyclization cascade of N-alkenylacrylamides is presented, providing a straightforward and chemoselective access to 1,3-dihydropyrrol-2-ones. In acrylamide-based radical cyclization, radical-trapping groups are mainly restricted to aryl, alkynyl or cyano group. But in this reaction, the enaminic double bond was used as an inbuilt radical trap, while the olefinic bond of the acrylamidyl moiety acted as the radical acceptor. Such chemoselectivity might be attributed to polarity matching.

Electroreductive synthesis of polyfunctionalized pyridin-2-ones from acetoacetanilides and carbon disulfide with oxygen evolution

“…Despite these exciting advances, the application of this O 2 evolution-enabled reduction strategy to the synthesis of more complex molecules remains untapped. As a part of our ongoing interest in green chemistry, 19 herein we report a copper-catalyzed, chemical reductant-free and electroreductive method for the synthesis of polyfunctionalized pyridin-2-ones from simple β-keto amides and CS 2 with O 2 evolution. This reaction is performed under mild electrolysis conditions, and the current, the copper catalyst and the base are all essential parameters.…”