Synthesis of β-hydroxy dithiocarbamate derivatives via regioselective addition of dithiocarbamate anion to epoxide in water

Abstract

The reactions of different dithiocarbamate anions with epoxides were investigated in water. With this method, β-hydroxy dithiocarbamate derivatives were synthesized in high yields. The reaction was also carried out in DMF in the presence of lithium perchlorate with a simple work-up procedure, and the results are compared.Key words: hydroxy dithiocarbamate, dithiocarbamate anion, epoxide, water.

Copper‐Catalyzed C−S Coupling of Quaternary Ammonium Salts and Dialkylcarbamodithioic Acid Salts

“…A); (ii) the reaction of alkyl halides and tetramethylthiuram disulfides, which are commonly prepared by the oxidative coupling of dialkylcarbamodithioic acid salts (Scheme , eq. B); (iii) the reaction of amines with expensive and toxic reagents, such as thiophosgene or isothiocyanate; and (iv) ring‐opening reactions of epoxides and N ‐tosyl aziridines with dialkylcarbamodithioic acid salts (Scheme , eq. C).…”

H2O‐Mediated Epoxide Ring‐Opening with Concomitant C–S Bond Formation: A One‐Pot Method to 3‐Hydroxy‐oxindolino‐dithiocarbamates as Cytotoxic Agents

“…In addition, the formation of dithiocarbamate involves certain limitation such as the use of toxic reagents, strong bases, long reaction time, low yields which encouraged us to search for more efficient methods for the synthesis of reactive dithiocarbamates from CS 2 and secondary amines. To the best of our knowledge, dithiocarbamate has not yet been explored as nucleophile perticularly in the isatin spiro ‐epoxide ring‐opening –. Moreover, the reaction proceeded in a one‐pot manner without using any base or catalyst and enable the use of water as the reaction medium, rather than organic solvents which makes this protocol more attractive in the context of green chemistry –.…”

One-pot three-component route for the synthesis of S-trifluoromethyl dithiocarbamates using Togni’s reagent

“…Beside traditional methods, a recent synthesis of dithiocarbamates via a one-pot reaction of an amine, CS 2 and an electrophile is of great interest due to its simplicity and environmental friendly procedure. Diverse electrophiles including alkyl halides [ 18 ], epoxides [ 19 ], alkenes [ 20 – 22 ], aldehydes [ 23 ], and alcohols [ 24 ] were applied for the synthesis of novel dithiocarbamates. Nevertheless, new synthetic methods towards dithiocarbamates are sought after and research in this area is still intense.…”