84353-56-0

Upstream product

• 354-38-1 2,2,2-trifluoroacetamide 
• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 84353-59-3 1-(2,2,2-trifluoroacetyl)-3-(E)-styrylurea 
• 33066-20-5 (E)-1-isocyanato-2-phenylethene 
• 76-05-1 trifluoroacetic acid 
• 84353-55-9 1-(2,2,2-trifluoroacetyl)-3-<2-(2,2,2-trifluoroacetyloxy)-2-phenylethyl>urea 

Downstream Products

• 90289-81-9 Demethoxytuberin 
• 118653-35-3 (S)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-N-((E)-styryl)-propionamide 
• 118653-26-2 [(S)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-propionyl]-((E)-styryl)-carbamic acid methyl ester 
• 118653-24-0 methyl(E)-N-formyl-N-(2-phenylethenyl)acetamide 
• 73885-72-0 trans-N-methoxycarbonyl-2-phenylethenylamine 
• 1722-84-5 (E)-N-styrylacetamide 
• 118653-16-0 (E)-N-acetyl-N-(2-phenylethenyl)acetamide 

Relevant academic research and scientific papers

Stereospecific One-pot Synthesis of Enamides and Enimides by the Copper Iodide Promoted Vinylic Substitution

Enamides and enimides were prepared stereospecifically from vinyl bromides by direct vinylic substitution in the presence of copper salt in aprotic polar solvents.

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.

Trifluoroacetylation and Subsequent Pyrolysis of 2-Amino-2-oxazolines

Treatment of 2-amino-5-phenyl-2-oxazoline (I) with trifluoroacetic anhydride gave 1,3-bis(2,2,2-trifluoroacetyl)-1-urea (II).Compound II was pyrolyzed at 120 deg C to give 2,2,2-trifluoroacetyl isocyanate (III) and 2,2,2-trifluoro-N-acetamide (IV).Compound II was readily hydrolyzed to give 1-(2,2,2-trifluoroacetyl)-3-urea (VI).Compound VI was pyrolyzed at 230 deg C to give 2,2,2-trifluoroacetamide (VII) and 2,2,2-trifluoro-N-(E)-styrylacetamide (VIII).It was considered that the formation of VIII proceeded through the intermediate 2-(2,2,2-trifluoroacetyloxy)-2-phenylethyl isocyanate (XI) or 1-(2,2,2-trifluoroacetyl)-3-(E)-styrylurea (XII), as shown in Chart 1.Keywords - 2-amino-2-oxazoline; trifluoroacetylation; pyrolysis; 1,3-bis(2,2,2-trifluoroacetyl)-1-alkylurea; O,N-bis(2,2,2-trifluoroacetyl)aminoethanol; 1-(2,2,2-trifluoroacetyl)-3-alkylurea; 1-(2,2,2-trifluoroacetyl)-3-alkenylurea