42063-41-2

Upstream product

• 134-20-3 2-carbomethoxyaniline 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 52693-18-2 2-[(2-carboxy-phenylamino)-methylene]-malonic acid diethyl ester 
• 74-88-4 methyl iodide 

Downstream Products

• 134-20-3 2-carbomethoxyaniline 
• 170152-23-5 ethyl 8-(4-chlorobenzoyl)-4-(o-tolylamino)quinoline-3-carboxylate 
• 170152-21-3 ethyl 8-(4-fluorobenzoyl)-4-(o-tolylamino)quinoline-3-carboxylate 
• 170152-22-4 ethyl 8-(4-methylbenzoyl)-4-(o-tolylamino)quinoline-3-carboxylate 
• 1442660-48-1 ethyl 8-benzoyl-4-(o-tolylamino)quinoline-3-carboxylate 
• 455889-15-3 3-ethyl 8-methyl 4-(o-tolylamino)quinoline-3,8-dicarboxylate 
• 1442660-45-8 ethyl 8-benzoyl-4-chloroquinoline-3-carboxylate 

Relevant academic research and scientific papers

Catalytic formation of ketones from unactivated esters through rhodium chelation-assisted C-O bond activation

A new method for building aryl aryl ketones containing heterocyclic rings through chelation-assisted C-O bond activation catalyzed by a rhodium complex has been developed. In this reaction, methyl quinoline-8-carboxylate, methyl quinoxaline-5-carboxylate, and their derivatives were reacted with an excess amount of a substituted phenyl boronic acid in the presence of a rhodium(I) complex to give substituted phenyl(quinolin-8-yl)methanone, phenylquinoxalin-5- ylmethanone, and their derivatives in medium to high yields. The current method offers a highly favorable synthetic pathway to efficiently build related drugs with an 8-benzoylquinoline core structure. This method may prove especially valuable for medicinal chemists for the late-stage introduction of versatile ketone moieties into complex scaffolds for diversity-oriented synthetic strategies.

2,2-Bis(ethoxycarbonyl)vinyl (BECV) as a versatile amine protecting group for selective functional-group transformations

A 2,2-Bis(ethoxycarbonyl) vinyl- (BECV) group was used for the selective protection of amines at room temperature in the presence of potentially interfering functional groups such as OH, SH, COOH as well as other NH 2 groups. Several functional group transformations such as esterification, O-alkylation, O-acylation, N-alkylation, N-acylation, S-alkylation can selectively be carried out in the presence of the BECV group. The selective deprotection of the BECV group was achieved in a short time using ethylenediamine at room temperature while several other functional groups such as benzoate, aliphatic esters, amides and ethers remain intact. The BECV group shows orthogonal stability against the common protecting groups such as Fmoc, Cbz and Boc.