118653-01-3

Upstream product

• 1011-54-7 2-methoxycinnamic acid 
• 118652-95-2 3-(2-methoxy-phenyl)-acryloyl azide 

Downstream Products

• 118653-31-9 N-[(E)-2-(2-Methoxy-phenyl)-vinyl]-acetamide 
• 118653-18-2 Acetyl-[(E)-2-(2-methoxy-phenyl)-vinyl]-carbamic acid methyl ester 
• 118653-13-7 2,2,2-Trifluoro-N-[(E)-2-(2-methoxy-phenyl)-vinyl]-acetamide 
• 118653-06-8 methyl(E)-N-2-(2-methoxyphenyl)ethenyl carbamate 

Relevant academic research and scientific papers

Synthesis of new N-(arylcyclopropyl)acetamides and N-(arylvinyl)acetamides as conformationally-restricted ligands for melatonin receptors

N-(Arylcyclopropyl)acetamides and N-(arylvinyl)acetamides or methyl ureas have been prepared as constrained analogues of melatonin. The affinity of these new compounds for chicken brain melatonin receptors and recombinant human MT1 and MT2 receptors was evaluated using 2-[ 125I]-iodomelatonin as radioligand. Strict ethylenic or cyclopropyl analogues of the commercialized agonist agomelatine (Valdoxan) were equipotent to agomelatine in binding bioassays. However, the ethylenic analogue was more effective than the cyclopropyl one in the melanophore aggregation bioassay, but was still less potent than the disubstituted 2,7-dimethoxy- naphtalenic compounds.

Synthesis of Enamides

(Z)-3-Arylprop-2-enoic acids can be converted by the Curtius procedure, through the acyl azides, into (Z)-2-arylethenyl isocyanates, which with methanol give methyl (Z)-N-(2-arylethenyl)carbamates.Acylation of the (Z)-enecarbamates, through their anions, leads to methyl (Z)-N-acyl-N-(2-arylethenyl)carbamates, which on treatment with lithium iodide in boiling N,N-dimethylformamide or acetonitrile undergo demethoxycarbonylation to give (Z)-enamides.The stereospecific route to enamides can also be used in the E-series.Treatment of (Z)- or (E)-2-arylethenyl isocyanates with trifluoroacetic acid gives (E)-N-(2-arylethenyl)trifluoroacetamides,the anions of which, with acylating agents, give (E)-enamides directly.