86896-38-0

Upstream product

• 36602-08-1 (N-methylanilino)acetonitrile 
• 104-87-0 4-methyl-benzaldehyde 
• 66985-49-7 2-(4-methylphenyl)-2-(trimethylsilyloxy)acetonitrile 
• 34966-53-5 methyl 4-methylphenylglyoxylate 
• 7163-50-0 (4-methylphenyl)(oxo)acetic acid 
• 100-61-8 N-methylaniline 
• 121-69-7 N,N-dimethyl-aniline 
• 94-08-6 4-methylbenzoic acid ethyl ester 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 103245-08-5 p-methyl-α-(N-methylanilino)-β-hydroxy-cinnamonitrile 

Relevant academic research and scientific papers

Silyl Cyanopalladate-Catalyzed Friedel-Crafts-Type Cyclization Affording 3-Aryloxindole Derivatives

3-Aryloxindole derivatives were synthesized through a Friedel-Crafts-type cyclization. The reaction was catalyzed by a trimethylsilyl tricyanopalladate complex generated in situ from trimethylsilyl cyanide and Pd(OAc) 2. Wide varieties of diethyl phosphates derived from N -arylmandelamides were converted almost quantitatively into oxindoles. When N, N -dibenzylamide was used instead of an anilide substrate, a benzo-fused δ-lactam was obtained. An oxindole product was subjected to substitution reactions to afford 3,3-diaryloxindoles with two different aryl groups.

Photoredox-Catalyzed Tandem Demethylation of N,N-Dimethyl Anilines Followed by Amidation with α-Keto or Alkynyl Carboxylic Acids

We report herein, a biomimetic approach for highly selective monodemethylation of N,N-dimethyl anilines to generate secondary amines and subsequent coupling with α-ketocarboxylic acids or alkynyl carboxylic acids to form α-ketoamides or alkynamides respectively under visible light photoredox catalyst in a single operation. From the deuterium-labeling experiment, it was probed that demethylation is the slowest step in this tandem process. Whereas, control experiments and spectroscopic studies revealed that photoredox catalyst is also involved in the subsequent amidation step. The reaction proceeds smoothly at room temperature providing moderate to excellent yield of the coupling products. The amides have also been converted to a series of biologically active spiro compounds. (Figure presented.).

AN EFFICIENT SYNTHESIS OF α-KETO AMIDES VIA REACTION OF α-(N-METHYLANILINO)-ACETONITRILE WITH ESTERS FOLLOWED BY HYDROLYSIS USING COPPER (II) ACETATE

An efficient sequence proposed for the conversion of esters to α-keto amides involves the reaction of α-(N-methylanilino)-acetonitrile with esters to afford β0hydroxy-α-cyanoenamines of which hydrolysis using copper (II) acetate gives the corresponding α-keto amides in good yields.