Copper-Catalyzed One-Pot N-Acylation and C5-H Halogenation of 8-Aminoquinolines: The Dual Role of Acyl Halides

J Org Chem. 2018 Mar 16;83(6):3403-3408. doi: 10.1021/acs.joc.8b00068. Epub 2018 Mar 7.

Abstract

The synthesis of N-acyl-5-halo-8-aminoquinolines has been realized by directly employing 8-aminoquinolines and acyl halides (Cl, Br, I) with copper catalysis. The construction of the target products involves domino N-acylation and C5-H halogenations of the 8-aminoquinoline, wherein the acyl halides act as the donors of both acyl and halide atoms, which enables the first access to the step efficient synthesis of 5-halogenated N-acyl quinlolines.

Publication types

  • Research Support, Non-U.S. Gov't