7474-18-2

Upstream product

• 606-83-7 3,3-Diphenylpropionic acid 
• 603-54-3 N,N-diphenylurea 
• 1669-73-4 1,3,3-triphenyl-propan-1-one oxime 
• 3056-73-3 N-phenylcinnamamide 
• 591-51-5 phenyllithium 
• 71-43-2 benzene 
• 3056-73-3 cinnamanilide 
• 102-92-1 cinnamoyl chloride 
• 62-53-3 aniline 
• 16717-64-9 1-azidostyrene 
• 91-01-0 1,1-Diphenylmethanol 
• 621-82-9 Cinnamic acid 
• 100-42-5 styrene 

Downstream Products

• 606-83-7 3,3-Diphenylpropionic acid 
• 50395-70-5 N,N-diphenylcinnamamide 

Relevant academic research and scientific papers

Silver-Catalyzed Decarboxylative Radical Addition/Cyclization of Oxamic Acids with Alkenes towards Quinolin-2-ones

An efficient silver-catalyzed tandem decarboxylative radical addition/cyclization of oxamic acids with alkenes has been developed. This method provides a novel and straightforward protocol toward a variety of 4-aryl-3,4-dihydroquinolin-2(1 H)-ones, 4-(α-c

NIS-mediated oxidative arene C(sp2)-H amidation toward 3,4-dihydro-2(1H)-quinolinone, phenanthridone, and N-fused spirolactam derivatives

A new radical-mediated intramolecular arene C(sp2)-H amidation of 3-phenylpropanamides or [1,1′-biphenyl]-2-carboxamides was developed to prepare a series of 3,4-dihydro-2(1H)-quinolinone and phenanthridone derivatives in moderate to excellent yields (33-94%). Spirolactams could also be obtained using this protocol.

Tandem superelectrophilic hydroarylation of CC bond and carbonyl reduction in cinnamides: Synthetic rout to 3,3-diarylpropylamines, valuable pharmaceuticals

Cinnamides ArCHCHCONRR′ in reactions with arenes Ar′H under the action of Bronsted (TfOH, FSO3H) or Lewis (AlBr3) superacids at rt for 1-2 h give CC bond hydroarylation products ArAr′CHCH2CONRR′ in yields of 63-98%. Reduction (LiAlH4/Et2O) of carbonyl group in the latter results in the formation of 3,3-diarylpropylamines ArAr′CHCH2CH2NRR′, valuable drugs. The reaction intermediates, superelectrophilic dications ArC+H-CH2C(OH+)NRR′, have been characterized by DFT calculations in terms of global electrophilicity index, natural charges, and atomic orbitals contributions.

Amide synthesis by nucleophilic attack of vinyl azides

A method for the synthesis of amide-containing molecules was developed using vinyl azides as an enamine-type nucleophile towards carbon electrophiles, such as imines, aldehydes, and carbocations that were generated from alcohols in the presence of BF3OEt2. After nucleophilic attack of the vinyl azide, a substituent of the resulting iminodiazonium ion intermediate migrates to form a nitrilium ion, which is hydrolyzed to afford the corresponding amide. Nitrilium intermediate: A new method for amide synthesis employs vinyl azides as enamine-type nucleophiles towards carbon electrophiles in the presence of BF3OEt2. After nucleophilic attack of the vinyl azide, a substituent of the resulting iminodiazonium ion intermediate A migrates to form nitrilium ion B, which is hydrolyzed to afford the corresponding amide.

Conjugate addition of RMgX-3MeLi to α,β-unsaturated amides and α,β-unsaturated carboxylic acids

In the presence of 3 equivalents of MeLi, various Grignard reagents reacted with secondary α,β-unsaturated amides and α,β-unsaturated carboxylic acids to give the corresponding Michael adducts in good yields. Copyright

Lewis acid catalyzed reaction of cinnamanilides: Competition of intramolecular and intermolecular Friedel-Crafts reaction

The first intermolecular Friedel-Crafts reaction of benzene leading to the formation of 3,3-diphenylpropionanilide 7 is described. 4-Methoxyaniline was reacted with cinnamoyl chloride to give 4-methoxycinnamanilide (5a), the treatment of which with aluminum (III) chloride in chlorobenzene at 120 °C or in benzene at 80 °C afforded exclusively 6-hydroxyquinolin-2(1H)-one (3a) or 4'-hydroxy-3,3-diphenylpropionanilide (7a), respectively. The formation of 7a rather than 3a in benzene indicated that an intermolecular Friedel-Crafts reaction occurred prior to the relatively more facile intramolecular ring cyclization. This intermolecular Friedel-Crafts reaction was observed during the attempted ring cyclization of cinnamanilide and its methoxy derivatives in aluminum (III) chloride/benzene. Preparation of 3a can also be achieved in 17% overall yield via the N-oxidation of 6-hydroxyquinoline followed by acetylation and hydrolysis.

CONJUGATE ADDITION OF ORGANOLITHIUM REAGENTS TO ACRYLANILIDE ANIONS

Phenyllithium, n-butyllithium, and t-butyllithium were found to add to substituted acrylanilide anions to give the 1,4-addition products in fair to good yields.