Acid-Promoted Cascade Reaction of N-(4-Chloroquinolin-3-yl)carbamates with Amines: One-Pot Assembly of Imidazo[4,5- c]quinolin-2-one

European J Org Chem. 2018 Apr 9;2018(13):1572-1580. doi: 10.1002/ejoc.201701772. Epub 2018 Feb 6.

Abstract

An acid-promoted cascade reaction of 4-chloroquinolin-3-yl carbamates with amines is described. This method achieves the formation of two new C-N bonds through an intermolecular amination/intramolecular cyclization reaction sequence. In combination with subsequent Suzuki coupling, this three-component telescopic procedure provides rapid access to various bioactive imidazo[4,5-c]quinolin-2-one derivatives.

Keywords: Acid-promoted reactions; Cyclization; Imidazo[4,5-c]quinolin-2-ones; Multicomponent reactions; One-pot synthesis.