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Synthesis of carboxylic dithiocarbamic anhydride and substituted thiourea derivatives in water

Author:
Azizi, Najmedin, Alipour, Masuomeh
Source:
Environmental chemistry letters 2018 v.16 no.4 pp. 1415-1421
ISSN:
1610-3653
Subject:
acetic anhydride, amines, carbon disulfide, isothiocyanates, organic halogen compounds, solvents, synthesis, thiourea
Abstract:
The use of water as a solvent has sometimes benefits such as improving reactivities and selectivities, simplifying work-up procedures, and environmentally benign. Many carboxylic dithiocarbamic anhydride products are valuable building blocks in heterocycles and natural products. Here we present a simple one-pot synthesis of carboxylic dithiocarbamic anhydride by condensation of amines, carbon disulfide, acyl halide, or acetic anhydride in water. We obtained a variety of biologically important acyl dithiocarbamate derivatives in 82–93% yields in 10–30 min. This procedure can be used for the synthesis of thioureas from dithiocarbamates. Here, the sequential, one-pot three-component reaction of amines, carbon disulfide, and isothiocyanates provides unsymmetrical substituted thioureas in 81–91% yields.
Agid:
6216050