Synthesis of functionalized 5-substituted thiazolidine-2-thiones via adscititious xanthate-promoted radical cyclization of allyl(alkyl/aryl)dithiocarbamates

Abstract

Functionalized 5-substituted thiazolidine-2-thiones were synthesized efficiently from alkyl allyl(alkyl/aryl)-dithiocarbamates via radical cyclization with the corresponding S-alkyl O-ethyl xanthates as the adscititious radical precursors. The application of the adscititious radical precursors improves not only the yields, but also the efficiency in the radical cyclization reaction significantly. The current adscititious radical precursor method provides a new strategy for the achievement and improvement of some radical reactions which are hardly or difficultly realized by the traditional direct methods.

Dearomatizing Naphthol Mannich Bases toward Spiro Thiazolidinethiones Catalyzed by Recyclable Reduced Graphene Oxide with Air as Oxidant

“… Thiazolidine-2-thiones are generally synthesized by heating alkaline solutions of β-aminothiols and carbon disulfide. Moreover, they have been afforded by cyclization of dithiocarbamate with the aid of excess SOCl 2 (or MsCl) and I 2 . , Recently, Gao et al synthesized functionalized 5-substituted thiazolidine-2-thiones from allyl­(alkyl/aryl)-dithiocarbamates with dilauroyl peroxide as a radical initiator, in which S -alkyl O -ethyl xanthates acted as the adscititious radical precursors . However, these methods still have some drawbacks, including the use of harmful reagents or catalysts, long reaction time, harsh reaction conditions, and unsatisfactory yields.…”

“…43,44 Recently, Gao et al synthesized functionalized 5substituted thiazolidine-2-thiones from allyl(alkyl/aryl)-dithiocarbamates with dilauroyl peroxide as a radical initiator, in which S-alkyl O-ethyl xanthates acted as the adscititious radical precursors. 45 However, these methods still have some drawbacks, including the use of harmful reagents or catalysts, long reaction time, harsh reaction conditions, and unsatisfactory yields. Therefore, the development of new sustainability-aimed methodology is of great importance.…”