86896-39-1

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 13305-14-1 methyl 2-hydroxy-2-(4-methoxyphenyl)acetate 
• 32766-61-3 4-methoxyphenylglyoxylate methyl ester 
• 7099-91-4 p-methoxybenzoylformic acid 
• 100-61-8 N-methylaniline 
• 121-69-7 N,N-dimethyl-aniline 
• 75681-30-0 1-(4-methoxyphenyl)-2-(methyl(phenyl)amino)ethan-1-one 
• 117177-66-9 2-(4-methoxyphenyl)-2-oxoacetyl chloride 
• 94-30-4 ethyl 4-methoxybenzoate 
• 36602-08-1 (N-methylanilino)acetonitrile 
• 103245-09-6 p-methoxy-α-(N-methylanilino)-β-hydroxy-cinnamonitrile 

Downstream Products

• 1268089-67-3 C₁₆H₁₇NO₃ 

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.).

Synthesis of α-Keto Amides by a Pyrrolidine/TEMPO-Mediated Oxidation of α-Keto Amines

A mild procedure has been developed for the synthesis of α-keto amides by α-oxidation of the corresponding α-keto amines mediated by pyrrolidine and TEMPO. The method can also be applied to the synthesis of α-keto thioamides and α-keto amidines.

Copper-catalyzed synthesis of azaspirocyclohexadienones from ∝-azido- N -arylamides under an oxygen atmosphere

A copper-catalyzed reaction of ∝-azido-N-arylamides was found to proceed under an oxygen atmosphere to afford azaspirocyclohexadienones. The present transformation is carried out by a sequence of denitrogenative formation of iminyl copper species from ∝-azido-N-arylamides and their imino-cupration with an intramolecular benzene ring on the amido nitrogen followed by consecutive formation of C-O bonds. The preliminary investigation revealed that molecular oxygen is a prerequisite for achieving the present catalytic cyclization and that one of the oxygen atoms of O2 was found to be incorporated into the cyclohexadienone moiety.

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.