40073-96-9

Upstream product

• 124-38-9 carbon dioxide 
• 52562-19-3 2-isopropenylaniline 
• 60249-97-0 1-(1-methylethenyl)-2-nitrobenzene 
• 552-89-6 2-nitro-benzaldehyde 
• 2258-42-6 formyl acetic anhydride 
• 551-93-9 2-aminoacetophenone 
• 64-18-6 formic acid 

Downstream Products

• 4789-76-8 4-methyl-2-phenylquinoline 
• 19155-24-9 3,3-dimethyloxindole 
• 30696-28-7 4-methyl-3,4-dihydroquinolin-2(1H)-one 
• 7117-17-1 N-methyl-2-(1-methylethenyl)benzenamine 
• 607-66-9 4-methyl-1,2-dihydroquinolin-2-one 
• 7654-51-5 2,2′-biquinoline-4,4′-dicarboxylic acid 
• 112158-32-4 1-isocyano-2-(1-methylethenyl)benzene 

Relevant academic research and scientific papers

The formation of quinolin-2(1H)-ones via electrocyclic reaction of o-isocyanatostyrenes generated in situ from o-isocyanostyrenes

A convenient one-pot preparation of 4-substituted or 3,4-disubstituted quinolin-2(1H)-ones from 2-isocyanostyrene derivatives, which involves mCPBA oxidation to the corresponding isocyanate intermediates followed by electrocyclization, is described.

Tetracoordinate borates as catalysts for reductive formylation of amines with carbon dioxide

We report sodium trihydroxyaryl borates as the first robust tetracoordinate organoboron catalysts for reductive functionalization of CO2. These catalysts, easily synthesized from condensing boronic acids with metal hydroxides, activate main group element-hydrogen (E-H) bonds efficiently. In contrast to BX3 type boranes, boronic acids and metal-BAr4 salts, under transition metal-free conditions, sodium trihydroxyaryl borates exhibit high reactivity of reductive N-formylation toward a variety of amines (106 examples), including those with functional groups such as ester, olefin, hydroxyl, cyano, nitro, halogen, MeS-, ether groups, etc. The over-performance to catalyze formylation of challenging pyridyl amines affords a promising alternative method to the use of traditional formylation reagents. Mechanistic investigation supports electrostatic interactions as the key for Si/B-H activation, enabling alkali metal borates as versatile catalysts for hydroborylation, hydrosilylation, and reductive formylation/methylation of CO2.

Mn(III)-Mediated Regioselective 6-endo-trig Radical Cyclization of o-Vinylaryl Isocyanides to Access 2-Functionalized Quinolines

A Mn(III)-mediated radical cyclization reaction of o-vinylaryl isocyanides and arylboronic acids or diphenylphosphine oxides to access various 2-functionalized quinolines under mild conditions was developed. With the introduction of radical stabilizing substituents (e. g. aryl and methyl group) on vinyl group, this reaction provides a regiospecific 6-endo-trig radical cyclization of o-vinylaryl isocyanides, giving a number of structurally unique and biologically potential 2-functionalized quinoline derivatives.

Synthesis of 3,3-disubstituted oxindoles through Pd-catalyzed intramolecular cyanoamidation

The cyanoamidation of olefins was achieved. When N-(2-vinylphenyl)cyanoformamides were treated with palladium catalyst, intramolecular cyanoamidation took place to give corresponding 3,3-disubstituted oxindoles. P(t-Bu)3 showed a remarkable eff

An Efficient Synthesis of 2,4-Disubstituted Quinolines by Electrophile-Mediated Cyclization Reactions of 2-Isocyanostyrene Derivatives

A novel quinoline synthesis starting with 2-isocyanostyrene derivatives is described. The treatment of 2-isocyanostyrene derivatives with aldehydes (or acetone) in the presence of a catalytic amount of diethyl ether-boron trifluoride afforded quinoline derivatives carrying a 1-hydroxyalkyl substituent at the 2-position. The use of acetaldehyde diethyl acetal or phenyloxirane as an electrophile under the same conditions gave the corresponding quinoline derivatives, carrying the 1-ethoxyethyl or 2-hydroxy-2-phenylethyl substituent at the 2-position, respectively. 2-Isocyanostyrene derivatives reacted with N,N-dimethyliminium salts without any catalyst to give 2-(1-dimethylaminoalkyl)quinolines.

Synthesis of 2,2′-biquinolines from o-isocyanostyrenes

The heating of o-isocyanostyrenes (1) in diglyme at reflux temperature for 2 h afforded the corresponding 2,2′-biquinolines (2) via a coupling/electrocyclic reaction in fair-to-good yields.