A Simple and Novel Eco‐Friendly Process for the One‐Pot Synthesis of Dithiocarbamates from Amines, Carbon Disulfide, and Epoxides.

Abstract

and Epoxides. -A simple and efficient one-pot reaction of epoxides (I), primary or secondary aliphatic amines (II) and carbon disulfide (III) under mild conditions (room temperature, solvent-free) provides access towards dithiocarbamates, e.g. (IV), in good yields. A single regioisomer is obtained for aliphatic (I) or alicyclic epoxides (V) while no significant regioselectivity is observed for styrene oxide (VII). -(AZIZI, N.; POURHASAN, B.; ARYANASAB, F.; SAIDI*, M. R.; Synlett 2007, 8, 1239-1242; Dep. Chem., Sharif Univ. Technol., Tehran, Iran; Eng.) -Mischke 38-057

Molecular Design, Synthesis, and Biological Evaluation of 2-Hydroxy-3-Chrysino Dithiocarbamate Derivatives

“…They can undergo regioselective ring opening from the less hindered terminal carbon side of the epoxide ring with a wide variety of nucleophiles by SN 2 reaction. The dithiocarbamate nucleophiles generated in situ from CS 2 and amines open the epoxide ring from the terminal carbon side [39,40,41] to afford 2-hydroxy dithiocarbamates, which are found to have a wide variety of applications in organic synthesis [42,43,44,45], pharmaceuticals [46,47,48,49], and agriculture [50,51,52].…”

A Facile and Efficient One-Pot Regioselective Synthesis of 2-Hydroxyalkyl Dithiocarbamates under Catalyst-Free Conditions

“…However, some of these procedures suffer from long reaction times, use of low temperatures, use of large excess of toxic carbon disulfide, use of strong basic conditions, and low to moderate yields of products. In two recent reports 2-hydroxy dithiocarbamates were directly prepared from primary or secondary amines, carbon disulfide and epoxides in acetone and in the presence of anhydrous potassium phosphate [41], and in catalyst-and solvent-free conditions [42]; in both methods, addition of an amine to CS 2 was slow, maintaining the temperature at around 0˚C followed by addition of an epoxide at room temperature.…”

“…They are usually synthesized by one of the following main methods: (1) reaction of an amine and carbon disulfide, to form dithiocarbamic acid salt, with epoxides [41,42], or with 2-hydroxyalkyl halides [43], and (2) reaction of amino-thiocarboxylic halides with 1,2-mercapto ethanol derivatives [44]. However, some of these procedures suffer from long reaction times, use of low temperatures, use of large excess of toxic carbon disulfide, use of strong basic conditions, and low to moderate yields of products.…”