Synthesis of S‐ and N‐Functionalized Dithiocarbamates from Cyclic Sulfates

Abstract

A novel methodology for the synthesis of S‐ and N‐functionalized dithiocarbamates starting from cyclic sulfates, amines and carbon disulfide by using different protocols, including microwave assistance and a multicomponent variant, has been developed. The procedure is highly versatile, simple and efficient.

Domino assembly of dithiocarbamatesviaCu-catalyzed denitrogenative thiolation of iodotriazole-based diazo precursors

“…Thus, a few bases were tested, and Et 3 N was established as the most suitable one (cf. entries 8 vs. [10][11][12]. Curiously enough, the less basic N,N-diethylaniline yielded the elimination byproduct 4 in an even higher amount (entry 12).…”

“…8 The most straightforward approaches are based on three-component reactions involving amines, CS 2 , and various reagents (Scheme 1A), e.g. alkyl halides, 9 benzyl alcohols, 10 epoxides, 11 cyclic sulfates 12 and sulfamidates, 13 vinyl ethers, 14 alkynes, 15 diazonium salts, 16 hypervalent iodine compounds, 17 arynes, 18 and Michael acceptors. 19 Cu-Assisted thiolation of aryl halides and boronic acids was proposed to access S -aryl dithiocarbamates.…”

Masked Thiol Sugars: Chemical Behavior and Synthetic Applications of S‐Glycopyranosyl‐N‐monoalkyl Dithiocarbamates

“…The starting materials per-O-acetylated-abromo lactose 1 D, [37] per-O-acetylated-N-acetyl-a-chloro glucosamine 1 B, [38] carbamodithioic acid N-[3-(triethoxysilyl)propyl] sodium salt 2 a, [39] S-(2,3,4,6-tetra-O-acetyl-b-d-glucopyranosyl)-N,N-diethyldithiocarbamate 3 Ad, [12a] dithiocarbamate 6, [26] and 1,2-O-isopropylidene-a-d-xylofuranose 3,5-cyclic sulfate 14 [33] were prepared according to reported procedures in the literature. TLC was performed with Merck silica gel 60 F254 aluminum sheets.…”

“…As expected, full consumption of the DTC sugar and transformation into the bis-glucosyl disulfide 4 A took place only for the N-monoalkyl DTC sugar 3 Ab, whereas in the case of the N-dialkyl DTC sugar 3 Ad the starting material was recovered intact. On the other hand, the xylofuranose DTC derivative 6 previously reported by us [26] that bears the S-linked N-monoalkyl dithiocarbamate functionality at the non-anomeric 5-position of the sugar was also exposed to TEA. Similarly to the case of compound 3 Ad, the starting material was recovered intact.…”

Design, Synthesis, Characterization and Biological Activities of Novel S‐(Acyloxy)butyl‐N,N‐Diethyldithiocarbamate Compounds

“…It is an inhibitor of such enzymes as cytochrome P450, it is a chelating agent for nickel and cadmium, it is a free-radical scavenger. [2] Diethyldithiocarbamate, a potent copper chelating agent, has long been used for the treatment of oxygen toxicity to the central nervous system, as an immunomodulator to treat cancer, and in HIV-infected patients. [3] A novel methodology for the synthesis of S-and N-functionalized dithiocarbamates starting by using different protocols, including microwave assistance and a multicomponent variant, has been developed.…”