Unprecedented thiocarbamidation of nitroarenes: a facile one-pot route to unsymmetrical thioureas

Abstract

A one-pot synthesis of unsymmetrical thiourea compounds was achieved by the reaction of nitroarenes with in situ generated dithiocarbamate anions.

Unprecedented Multicomponent Reaction of Indoles, CS2 and Nitroarenes: Stereoselective Synthesis of (Z)‐3‐((Arylamino)methylene)indoline‐2‐thiones

“…Although the detailed reaction mechanism of this transformation is unclear at this stage, a plausible reaction pathway for this reaction is proposed in Scheme 6 based on our preliminary observations and the previous literatures [5,6] . Initially, N ‐methylindole 1 reacted with CS 2 to give a 2‐thiol‐3‐carbodithioic acid B via the intermediate A .…”

“…Recently, Saha et al. developed a facile one‐pot thiocarbamidation of nitroarenes with CS 2 and amines to produce unsymmetrical thiourea compounds (Scheme 1, b) [6] . Various cyclic and acyclic amines reacted with CS 2 to form dithiocarbamate anions which reacted with nitroarenes and produced the unsymmetrically substituted thioureas in good yields.…”

Chiral Thioureas—Preparation and Significance in Asymmetric Synthesis and Medicinal Chemistry

“…In 2019, a route to unsymmetrical thioureas was proposed by Dutta et al involving the reaction of dithiocarbamate anions, generated in situ from secondary or primary amines and carbon disulfide at low temperature, with aromatic nitro compounds (Scheme 12) [78]. DMF as solvent, potassium carbonate as a base, and temperature of 100 • C were established as optimal conditions for the second step of the reaction.…”

“…Scheme 12. Preparation of thioureas from nitro compounds, carbon disulfide and amines [78]. Scheme 13.…”

“…1-(Methyldithiocarbonyl)imidazole and its quaternary Nmethylated salt were found by Mohanta et al to be effective thiocarbonyl transfer agents which Scheme 12. Preparation of thioureas from nitro compounds, carbon disulfide and amines [78].…”