130474-03-2

Upstream product

• 101-97-3 Ethyl 2-phenylethanoate 
• 62001-37-0 N-benzotriazol-1-ylmethyl-4-methyl-aniline 
• 1309606-64-1 3-hydroxy-2-phenyl-N-p-tolylpropanamide 
• 106-49-0 p-toluidine 
• 78935-61-2 (Z)-((1-ethoxy-2-phenylvinyl)oxy)trimethylsilane 
• 130473-95-9 2-Phenyl-3-p-tolylamino-propionic acid ethyl ester 

Downstream Products

• 1309606-58-3 6-methyl-3-phenyl-2,3-dihydroquinolin-4(1H)-one 

Relevant academic research and scientific papers

Synthesis of 2,3-dihydro-4(1H)-quinolones and the corresponding 4(1H)-quinolones via low-temperature fries rearrangement of N-arylazetidin-2- ones

N-Arylazetidin-2-ones of the general form 1, which are readily prepared by GoldbergBuchwald-type copper-catalyzed coupling of N-unsubstituted azetidin-2-ones with the relevant aryl halide or using Mitsunobu cyclization processes, undergo smooth Fries-rearrangement in triflic acid at 018°C to give the isomeric 2,3-dihydro-4(1H)-quinolones (2). Dehydrogenation of the latter compounds using 10% Pd on C in 1.0M aqueous sodium hydroxide/propan-2-ol mixtures at ca. 82°C provides the corresponding 4(1H)-quinolones (3).

Preparation of β-aminoesters from ketene silyl acetals and N-(alkylamino)benzotriazoles

A wide variety of β-aminoesters are prepared in good yields by the reaction of lithium ester enolates derived from ketene silyl acetals with N-(alkylamino)benzotriazoles. The secondary β-aminoesters readily cyclize to β-lactams (2-azetidinones) on deprotonation.