17463-82-0

Upstream product

• 2181-42-2 trimethylsulphonium iodide 
• 2286-29-5 ethyl 2-cyano-3-(4-methoxyphenyl)prop-2-enoate 
• 105-56-6 ethyl 2-cyanoacetate 
• 100-06-1 1-(4-methoxyphenyl)ethanone 

Downstream Products

• 15854-11-2 ethyl 2-amino-4-(4'-methoxyphenyl) thiophene-3-carboxylate 
• 86945-21-3 3-(4-Methoxyphenyl)-1-butylamin 
• 55755-77-6 α-Methyl-α-<4-methoxy-phenyl>-bernsteinsaeuredinitril 
• 1149-92-4 Methyl-2-cyano-3-(p-methoxyphenyl)-3-methylbutanoat 

Relevant academic research and scientific papers

Efficient synthesis of substituted 2-amino-3-carbethoxythiophenes

A microwave-assisted method for the synthesis of a variety of thiophene o-aminoesters (2a-l) has been developed, starting from an appropriate aldehyde, methyl ketone or acetoacetate ester with ethyl cyanoacetate in the presence of elemental sulfur. Copyright Taylor & Francis Group, LLC.

The unprecedented reaction of dimethylsulfonium methylide with Michael acceptors: Synthesis of 1-substituted vinyl silanes and styrenes

Rather than the usual cyclopropanation, conditions for an unprecedented elimination reaction from the adduct of dimethylsulfonium methylide and various Michael acceptors have been established leading to functionalized 1-substituted alkenes. In silyl substituted substrates (2a and 2h), where a facile Peterson-type olefination is possible from the adduct; elimination took place instead to give functionalized 1 -substituted vinyl silanes. Aryl substituted Michael acceptors (2b-e, 2g and 2i-k) also underwent a similar kind of olefination to give 1-substituted styrene derivatives with moderate yields along with a side product, which arose by nucleophilic demethylation from the adduct of dimethylsulfonium methylide and arylidene malonates. Hammett studies revealed that selectivity for olefination vs. demethylation increases as the aryl substituent becomes more electron deficient. Alkylidene malonates (2f and 2l) with a β-alkyl substituent did not favour the olefination process. Sequential addition of Michael acceptors and alkyl halides to a mixture of dimethylsulfonium methylide and sodium dimsylate provided olefination followed by alkylation on the active methine group. A mechanistic pathway has been formulated from the studies of a few sulfonium methylides. The Royal Society of Chemistry 2005.

Pharmaceutically active compounds and methods of use

New fused thiophene compounds are provided and methods of using those compounds for a variety of therapeutic indications. Compounds of the invention are particularly useful for treatment of neuropathic pain.