Tandem Alkylation/Michael Addition Reaction of Dithiocarbamic Acids with Alkyl γ-Bromocrotonates: Access to Functionalized 1,3-Thiazolidine-2-thiones

Abstract

Thiazolidine-2-thiones were prepared via a novel multicomponent reaction of primary amines (amino acids), carbon disulfide and γ-bromocrotonates. The reaction proceeds via a domino alkylation/intramolecular Michael addition to provide the corresponding thiazolidine-2-thiones in high to excellent yields. Using diamines in this protocol, bis(thiazolidine-2-thiones) derivatives were synthesized. The synthetic utility of adducts was demonstrated by hydrolysis, amidation and oxidation reactions.

Facile access to S-methyl dithiocarbamates with sulfonium or sulfoxonium iodide as a methylation reagent

“…10 A classical strategy for their preparation is through one-pot condensation of dithiocarbamic acid, which was generated in situ by mixing an amine and CS 2 , with electrophiles such as alkyl halides and diazonium salts. 11 Herein, based on this reaction, we verified that trimethylsulfonium iodide ((CH 3 ) 3 SI) could be an efficient methylation reagent for the synthesis of S -methyl dithiocarbamates starting from secondary amines. Furthermore, the methylation reagent was extended to trimethylsulfoxonium iodide ((CH 3 ) 3 SOI, TMSO-I) for the preparation of S -methyl dithiocarbamates starting from both primary and secondary amines.…”

A Decade of Advances of CS2/Amines in Three-Component Reactions

“…Finally, an acceptor accomplishes the intramolecular cyclization to give 10.1 . The use of esters, 13` b c acids, 13d ketones, 13e f and nitriles, 13g as the acceptor have all been studied. This represents a facile route to thiazolidine heterocycles, as usually no catalyst or additive base is required.…”