93501-31-6

Upstream product

• 872782-55-3 3-hydroxy-3,3-diphenyl-propionic acid p-toluidide 
• 4456-79-5 3,3-diphenylacryloyl chloride 
• 106-49-0 p-toluidine 
• 93501-18-9 N-p-Tolyl-2-bromo-3,3-diphenylpropanamide 
• 93500-92-6 N-p-tolyl-α,β-dibromohydrocinnamamide 
• 71-43-2 benzene 
• 1522-14-1 1,1-diphenyl-3-(p-tolyl)prop-2-yn-1-ol 
• 766-97-2 4-n-methylphenylacetylene 

Downstream Products

• 93501-05-4 6-methyl-4,4-diphenyl-3,4-dihydroquinolin-2(1H)-one 
• 70453-82-6 6-methyl-4-phenyl-1,2-dihydroquinolin-2-one 

Relevant academic research and scientific papers

Lewis Acid Mediated Tandem Reaction of Propargylic Alcohols with Hydroxylamine Hydrochloride to Give α,β-Unsaturated Amides and Alkenyl Nitriles

We have developed a highly selective method for the synthesis of α,β-unsaturated amides and alkenyl nitriles from readily available propargylic alcohols. The reaction proceeded smoothly under the neutral conditions with hydroxylamine hydrochloride (NH2OH·HCl) as the nitrogen source. The development of these new strategies has significantly extended the application of hydroxylamine hydrochloride to the chemistry of propargylic alcohols. Moreover, both secondary and tertiary alcohols have been highly regioselectively transformed to the desired products with good functional group compatibility.

TMSCl-mediated synthesis of α,β-unsaturated amides via C-C bond cleavage and C-N bond formation of propargyl alcohols with trimethylsilyl azide

A new method with high efficiency for the synthesis of α,β- unsaturated amides from the easily prepared propargyl alcohols and TMSN 3 using TMSCl as an acid promoter is developed. A wide variety of α,β-unsaturated amides were produced in moderate to excellent yields. Mechanistic studies indicate that this transformation involves TMSCl-mediated allenylazide intermediate formation, C-C bond cleavage, and C-N bond formation. Significantly, this reaction shows good functional group compatibility and high regioselectivity, with a relatively short reaction time and inexpensive reagents.

A New Route for the Synthesis of Coumarins, Thiacoumarins and Carbostyrils

3-Arylcarbostyrils, coumarins and thiacoumarins (3) have been prepared from the respective β-aryl-α-bromodihydrocinnamoyl derivatives (2) by treatment with AlCl3.The β,β-diarylacrylic acid derivatives (4) and (9), obtained from 2, on reaction with AlCl3 afford 4-arylcarbostyrils (5) 6-methyl-4-phenylthiacoumarin (10) respectively.However the oxygen analogs (11) give 3,3-diphenyl-1-indanone (12)