28925-45-3

Upstream product

• 75-15-0 carbon disulfide 
• 100-51-6 benzyl alcohol 
• 74-88-4 methyl iodide 
• 74734-11-5 1H-imidazole-1-carbodithioic acid methyl ester 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 766-92-7 [(methylthio)methyl]-benzene 
• 624-92-0 Dimethyldisulphide 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 868-84-8 S,S-dimethyl dithiocarbonate 
• 13049-99-5 S-Benzyl S-methyl dithiocarbonate 
• 26504-28-9 dithiocarbonic acid S,S'-dibenzyl ester 
• 350-50-5 benzyl fluoride 
• 588-59-0 stilbene 
• 478189-98-9 4-methyl-3-oxothiopentanoic acid O-benzyl ester 
• 678994-78-0 3-(4-methoxyphenyl)-3-oxothiopropionic acid O-benzyl ester 
• 176729-59-2 O-benzyl acetothioacetate 
• 1215-52-7 N-benzoyl-N'-benzylhydrazine 
• 57260-70-5 4-benzyl-piperazine-1-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Aryl Radical Activation of C-O Bonds: Copper-Catalyzed Deoxygenative Difluoromethylation of Alcohols

Given their ubiquity in natural products and pharmaceuticals, alcohols represent one of the most attractive starting materials for the construction of C-C bonds. We report herein the first catalytic strategy to harness the reactivity of aryl radicals for the activation of C-O bonds in alcohol-derived xanthate esters, allowing for the discovery of the first catalytic deoxygenative difluoromethylation reaction. Under copper-catalyzed conditions, a wide variety of alkyl xanthate esters, readily synthesized from alcohol feedstocks, were activated by catalytically generated aryl radicals and were converted to the alkyl-difluoromethane products via alkyl radical intermediates. This scalable protocol exhibits a broad substrate scope and functional group tolerance, enabling late-stage modification of complex pharmaceutical agents. A one-pot protocol has been developed that allows for the direct use of free alcohols without purification of the xanthate esters. Mechanistic studies are consistent with the hypothesis of aryl radicals being formed and initiating the cleavage of the C-O bonds of xanthate esters, to generate alkyl radicals as the key intermediates. This aryl radical activation approach represents a new strategy for the activation of alcohols as cross-coupling partners.

Ni-Catalyzed Synthesis of Thiocarboxylic Acid Derivatives

A Ni-catalyzed cross-coupling of readily accessible O-alkyl xanthate esters or thiocarbonyl imidazolides and organozinc reagents for the synthesis of thiocarboxylic acid derivatives has been developed. This method benefits from a fast reaction time, mild reaction conditions, and ease of starting material synthesis. The use of transition-metal catalysis to access a diverse range of thiocarbonyl-containing compounds provides a useful complementary approach when compared with previously established methodologies.

Base-Induced Cyclization of Active Methylene Isocyanides with Xanthate Esters: An Efficient Method for the Synthesis of 5-Alkoxy-4-(tosyl/ethoxycarbonyl)-1,3-thiazoles

Sodium hydride-induced cyclization of 1-[(isocyanomethyl)sulfonyl]-4-methylbenzene or ethyl isocyanoacetate with various xanthate esters gave 5-alkoxy-4-tosylthiazoles or ethyl 5-alkoxythiazol-4-ylcarboxylates, respectively, in good to excellent yields. The xanthate ester S -methyl O -phenyl dithiocarbonate gave 5-(methylsulfanyl)-4-tosyl-1,3-thiazole when treated with 1-[(isocyanomethyl)sulfonyl]-4-methylbenzene under similar conditions.

Superoxide ion-promoted facile one-pot synthesis of O-alkyl-S-methyl dithiocarbonates from alcohol under mild reaction conditions

A new, mild, and efficient protocol for the one-pot synthesis of O-alkyl-S-methyl dithiocarbonates (xanthates) has been described in reasonably good yields from a variety of alcohols employing carbon disulfide and methyl iodide using superoxide ion at room temperature. Copyright Taylor & Francis Group, LLC.

An efficient, one-pot, Triton-B catalyzed synthesis of O-alkyl-S-methyl dithiocarbonates

A novel process for the one-step conversion of a variety of primary and secondary alcohols into their O-alkyl-S-methyl dithiocarbonates using methyl iodide catalyzed by the Triton-B/CS2 system was developed. Thus, O-alkyl-S-methyl dithiocarbonates were obtained in very good to excellent yields. This protocol is mild and efficient compared to other methods.

GLYCOPYRANOSYLOXYPYRAZOLE DERIVATIVES AND MEDICINAL USE THEREOF

The present invention provides glucopyranosyloxypyrazole derivatives represented by the general formula: wherein R1, R2 and R3 represent a hydrogen atom or a halogen atom; R4 represents a lower alkyl group or a halo(lower alkyl) group; and R5 represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkylthio group, etc., a pharmaceutically acceptable salt thereof or a prodrug thereof., which exert an excellent inhibitory activity in human SGLT2, and therefore are useful as drugs for the prevention or treatment of a disease associated with hyperglycemia such as diabetes, diabetic complications or obesity, pharmaceutically acceptable salts thereof or prodrugs thereof, production intermediates thereof and pharmaceutical uses thereof.

Mild and efficient synthesis of thiocarbonates and thiocarbamates via a three-component coupling utilizing Cs2CO3 and TBAI

The presence of cesium carbonate and tetrabutylammonium iodide (TBAI) facilitated efficient thiocarbonylation of alcohols, and thiocarbamation of amines, using carbon disulfide with alkyl halides. This protocol was mild, chemoselective, and efficient, compared to the existing methods.

1-(Methyldithiocarbonyl)imidazole: A Reagent of S-Methyldithiocarbonylation

The development, synthesis and use of the 1-(methyldithiocarbonyl)imidazole as a reactive reagent for the mild conversion of alcohols to O-alkyl, S-methyl dithiocarbonates is reported.

Potassium fluoride on alumina: A convenient synthesis of O-alkyl methyldithiocarbonates. Pyrolysis of O-benzyl-S-methyldithiocarbonates

Xanthates were easily prepared by adsorption of alcohol on KF-Al2O3 followed by treatment of carbon disulfide and iodomethane at room temperature. Pyrolysis of benzyl xanthate affords to a complex mixture of products. A radical process was proposed to explain the nature of products obtained.

ONE POT TRANSFER SYNTHESIS OF O-ALKYL, S-METHYL DITHIOCARBONATES (XANTHATES)

O-Alkyl, S-methyl dithiocarbonates of phenol, benzyl, primary and secondary alcohols were prepared in a one pot procedure under phase transfer catalysis conditions.