One-pot synthesis of S-alkyl dithiocarbamates via the reaction of N-tosylhydrazones, carbon disulfide and amines

Abstract

A new, convenient and efficient transition metal-free synthesis of S-alkyl dithiocarbamates through one-pot reaction of N-tosylhydrazones, carbon disulfide and amines is reported. Tosylhydrazones derived from various aromatic and aliphatic ketones or aldehydes were tested and gave dithiocarbamates in good to excellent yields. The tosylhydrazones can be generated in situ without isolation, which provides a simpler one-pot method to synthesize dithiocarbamates via the reaction of carbonyl compounds, carbon disulfide and amines in the presence of 4-methylbenzenesulfonohydrazide.

Luxury of N‐Tosylhydrazones in Transition‐Metal‐Free Transformations

“…[101] This reactionr eadily allows the synthesis of an array of dithiocarbamates 175 from a one-pot reactiono fN-tosylhydrazones,c arbon disulfide and secondary amines.T he optimized conditions were broadly applicable to the tosylhydrazones of aryl and alkyl aldehydes,a sw ella sa ryl ketones and resulted in the corresponding products in good yields. [101] This reactionr eadily allows the synthesis of an array of dithiocarbamates 175 from a one-pot reactiono fN-tosylhydrazones,c arbon disulfide and secondary amines.T he optimized conditions were broadly applicable to the tosylhydrazones of aryl and alkyl aldehydes,a sw ella sa ryl ketones and resulted in the corresponding products in good yields.…”

“…In 2013, Sha and Weir eported aw ell-designed approach for the synthesis of S-alkyl dithiocarbamates 175 in the absence of transitionm etals (Scheme 90). [101] This reactionr eadily allows the synthesis of an array of dithiocarbamates 175 from a one-pot reactiono fN-tosylhydrazones,c arbon disulfide and secondary amines.T he optimized conditions were broadly applicable to the tosylhydrazones of aryl and alkyl aldehydes,a sw ella sa ryl ketones and resulted in the corresponding products in good yields. However, the reactionw ith aromatic aminesf ailed due to the poor nucleophilicity for reactionw ith CS 2 .…”

“…In 2013, Sha and Wei reported a well‐designed approach for the synthesis of S ‐alkyl dithiocarbamates 175 in the absence of transition metals (Scheme ) . This reaction readily allows the synthesis of an array of dithiocarbamates 175 from a one‐pot reaction of N ‐tosylhydrazones, carbon disulfide and secondary amines.…”

Dithiocarbamates: Challenges, Control, and Approaches to Excellent Yield, Characterization, and Their Biological Applications

“…Bases are incorporated to conserve the amines [8]. General method of preparation is called one-pot synthesis, where the synthesis reactions can be seen in equations (1) and (2) [9]. The two approaches to synthesis are the insertion reaction approach and replacement (substitution) reaction approach [10–12].…”

Progress in the Studies on Synthesis and Biological Properties of Dithiocarbamates

“…1.2.4 碳酸钾作用下的合成方法 2013 年, 魏运洋课题组 [24] 报道了碳酸钾作催化剂, 2009 年, Srivastava 等 [29] 报道了一种合成(E)-和(Z)- 2011 年, Karmakar 课题组 [31] 以水为溶剂, 采用 MgO 纳米晶体催化胺、 二硫化碳与 α,β-不饱和化合物反 应, 快速高效地合成相应的氨基二硫代甲酸酯衍生物 (Eq. 14).…”