549500-24-5

Upstream product

• 123-62-6 propionic acid anhydride 
• 2835-77-0 (2-aminophenyl)(phenyl)methanone 
• 100-52-7 benzaldehyde 
• 60751-75-9 N-(2-iodophenyl)propionamide 
• 620-71-3 N-(phenyl)-2-methylacetamide 
• 108-88-3 toluene 
• 690661-10-0 heptanoic acid (2-benzoyl-phenyl)-amide 
• 79-03-8 propionyl chloride 

Downstream Products

• 107288-91-5 2-ethyl-4-phenylquinazoline 
• 5260-41-3 2-ethyl-3-phenyl-3H-quinazolin-4-one 
• 78825-91-9 2-ethyl-3-phenyl-1H-indole 
• 88795-69-1 1-Ethyl-3-methyl-4-phenyl-1H-quinolin-2-one 
• 37118-75-5 3-methyl-4-(phenyl)-2-(1H)-quinolinone 
• 690661-10-0 heptanoic acid (2-benzoyl-phenyl)-amide 
• 2835-77-0 (2-aminophenyl)(phenyl)methanone 

Relevant academic research and scientific papers

Palladium Catalyzed Direct Acylation of Iodo-Acetanilides/Iodo-Phenyl Acetates: Domino One-Pot Synthesis of 2-Quinolinones

Pd-catalyzed direct acylation reaction of iodoacetanilides/iodophenyl acetates with aldehydes is presented. Simple, bench-top aldehydes were used as non-toxic acylating agents. This protocol comprises direct coupling with aldehydes without activating the carbonyl group and without directing group assistance. The strategy was applied to a domino one-pot synthesis of 2-quinolinones through acylation and intramolecular aldol condensation. Significantly, the strategy was extended to the domino one-pot synthesis of drugs and bioactive compounds.

Palladium-catalyzed direct oxidative ortho-acylation of anilides with toluene derivatives

Direct oxidative ortho-acylation reaction of anilides with toluene derivatives in the presence of palladium acetate using tert-butyl hydroperoxide as an oxidant was developed. A broad range of diaryl ketones was obtained in good to excellent yields (up to 95%). The plausible mechanism was also proposed.

Palladium-catalyzed direct ortho -acylation through an oxidative coupling of acetanilides with toluene derivatives

A facile ortho-acylation of acetanilides by a Pd-catalyzed oxidative C-H activation was developed in which low toxic, stable, and commercially available toluene derivatives were first used as acylation reagents by a tandem reaction to form o-acylacetanili

Facile synthesis of 4-phenylquinolin-2(1H)-one derivatives from N-acyl-o-aminobenzophenones

An efficient synthesis of 4-phenylquinolin-2(1H)-one derivatives has been achieved in a one-pot reaction from N-acyl-o-aminobenzophenones 1a-c (a: acyl=acetyl; b: acyl=propanoyl; c: acyl=heptanoyl) using NaH as a base. Treatment of 1 with NaH provided the quinolones 2a-c with 62-83% yields, whereas the reaction in the presence of alkyl iodide (alkyl=methyl, ethyl, n-octyl) gave the corresponding N-alkylated quinolones 3a-g in 75-95% yields. The alkylation reaction of 4-phenylquinolin-2(1H)-one 2a with alkyl halide gave a mixture of N-alkylated and O-alkylated products. Comparison of IR and NMR data of the N-alkylated and O-alkylated compounds with those of 2a-c indicated that 2a-c exist as the lactam form.