50507-86-3

Upstream product

• 21954-69-8 diethyl-amidosulfurous acid methyl ester 
• 104-03-0 4-nitrobenzeneacetic acid 
• 111512-98-2 N,N-diethylamino(p-nitro-phenyl)acetylene 
• 109-89-7 diethylamine 
• 51738-10-4 2,2-dibromo-1-(4-nitrophenyl)ethene 
• 50434-36-1 4-nitrophenylacetyl chloride 
• 2430-01-5 2-bromo-N,N-diethylacetamide 
• 586-78-7 para-nitrophenyl bromide 
• 4203-31-0 2-diazo-1-(4-nitrophenyl)ethanone 
• 121-44-8 triethylamine 
• 58784-38-6 4-nitrophenylketene 
• 1497283-55-2 C₁₂H₁₆N₂O₃ 
• 940-13-6 1-(2-bromoethynyl)-4-nitrobenzene 
• 555-16-8 4-nitrobenzaldehdye 

Downstream Products

• 1665-60-7 diethyl-(4-amino-phenethyl)-amine 
• 5345-22-2 diethyl-(4-nitro-phenethyl)-amine 

Relevant academic research and scientific papers

Direct amidation of carboxylic acids with tertiary amines: Amide formation over copper catalysts through C-N bond cleavage

A copper-catalyzed system for the amidation of carboxylic acids with tert-amines through C-N bond cleavage was developed. This protocol is practical and represents a simple way to produce functionalized amides from basic starting materials in moderate to good yields. A plausible mechanism is proposed for the reaction. Copyright

Ketene reactions with tertiary amines

Tertiary amines react rapidly and reversibly with arylketenes in acetonitrile forming observable zwitterions, and these undergo amine catalyzed dealkylation forming N,N-disubstituted amides. Reactions of N- methyldialkylamines show a strong preference for methyl group loss by displacement, as predicted by computational studies. Loss of ethyl groups in reactions with triethylamine also occur by displacement, but preferential loss of isopropyl groups in the phenylketene reaction with diisopropylethylamine evidently involves elimination. Quinuclidine rapidly forms long-lived zwitterions with arylketenes, providing a model for catalysis by cinchona and related alkaloids in stereoselective additions to ketenes.

Amination of phenylketenes. Substituent effect on amine-catalyzed tautomerization of amide enol

The transient intermediates with infrared bands at 1676-1680 cm -1 observed for reaction of substituted phenylketenes with diethylamine in acetonitrile were suggested to be the amide enols rather than the zwitterions on the basis of the theoretical calculations. A single broad band at 1674 cm-1 observed for reaction with the primary amines was attributed to overlap of two bands of the intermediate (amide enol) and the final product (amide). The substituent effect for the second-order rate constants of diethylamine-catalyzed tautomerization of the amide enol intermediates to give the amides was analyzed successfully by the Yukawa-Tsuno equation, giving a ρ value of 0.63 and an r- value of 1.31. The r- value larger than unity for pKa of phenols indicates that the negative charge formed at an oxygen atom of the amide enol at the transition state is significantly delocalized into the aromatic π-system through the ethenyl group. This r- value was considered to reflect an intrinsic property of β-phenylenolate skeleton. A remarkably small ρ value attributes to the cyclic transition structure where the negative charge disperses in a six-member ring. Copyright 2013 John Wiley & Sons, Ltd. The substituent effect for the reaction of the amide enol intermediate generated from phenylketene with diethylamine has been analyzed. The large r- of 1.31 was attributed to an intrinsic property of β-phenylenolate skeleton. A remarkably small ρ of 0.63 suggested the cyclic transition structure. Copyright

Synthesis and biological evaluation of new 4β-anilino-4′-O- demethyl-4-desoxypodophyllotoxin derivatives as potential antitumor agents

A series of new 4β-anilino-4′-O-demethyl-4-desoxypodophyllotoxin derivatives were prepared and evaluated for their cytotoxicities against four human cancer cell lines including KB, KB/VCR, A549 and 95D. Most compounds showed better growth-inhibition activities against tested cell lines than that of etoposide (VP-16). Preliminary structure-activity relationships (SARs) were concluded and it indicated that the side chains substituted at 4β position of podophyllotoxin significantly influenced the cytotoxic activity, especially for the drug resistance profile. In vivo studies of compound 26c on highly metastatic human lung cancer xenograft in nude mice showed that it can significantly inhibit tumor growth with administrating by oral route.

Palladium-catalyzed intermolecular α-arylation of zinc amide enolates under mild conditions

The intermolecular α-arylation and vinylation of amides by palladium-catalyzed coupling of aryl bromides and vinyl bromides with zinc enolates of amides is reported. Reactions of three different types of zinc enolates have been developed. The reactions of

On the Synthesis and Basicity of 1,3-Diaminoisoquinolines

A series of 6- and 7-substituted derivatives of 1,3-diaminoisoquinoline were synthesized by the reaction of N,N-diethylarylacetamides with POCl 3 and then with N,N-dimethylcyanamide. The products were identified by means of spectroscopic methods and their pKa dissociation constants were determined.

An efficient method for one-carbon elongation of aryl aldehydes via their dibromoalkene derivatives

Various aryl aldehydes were efficiently converted into one-carbon extended aryl acetamides or aryl acetic acids through the reaction of their dibromoalkene derivatives with pyrrolidine in the presence of water under very mild conditions.

SYNTHESIS OF 1-(ARYLETHYNYL)AZIRIDINES

Studies have been made on the possible synthesis of 1-(arylethynyl)aziridines by oxidative condensation of phenylacetylene with aziridine and by alkylation of aziridine with 1-halo-2-arylacetylenes.