Domino assembly of dithiocarbamates<i>via</i>Cu-catalyzed denitrogenative thiolation of iodotriazole-based diazo precursors

Abstract

An efficient domino approach to assemble benzoxazoles and anthranilamides bearing dithiocarbamate moieties has been developed. The proposed route represents a Cu-catalyzed three-component reaction between readily available 5-iodo-1,2,3-triazoles, amines, and CS₂. The cascade transformation is based on a denitrogenative coupling of <i>in situ</i> formed dithiocarbamic acids with diazo intermediates, generated <i>via</i> annulation-triggered triazole ring-opening. This method is applicable to nucleophilic secondary amines and features good functional group compatibility.