7542-92-9

Upstream product

• 922-67-8 propynoic acid methyl ester 
• 100-61-8 N-methylaniline 
• 125735-87-7 1-diazo-5-(methylphenylamino)pentane-2,5-dione 
• 96-32-2 bromoacetic acid methyl ester 
• 93-61-8 N-methyl-N-phenylformamide 
• 33684-12-7 4-oxo-4-(N-methylphenylamino)butanoic acid 
• 292638-85-8 acrylic acid methyl ester 

Relevant academic research and scientific papers

Electrosynthesis of Dihydropyrano[4,3-b]indoles Based on a Double Oxidative [3+3] Cycloaddition

Oxidative [3+3] cycloadditions offer an efficient route for six-membered-ring formation. This approach has been realized based on an electrochemical oxidative coupling of indoles/enamines with active methylene compounds followed by tandem 6π-electrocyclization leading to the synthesis of dihydropyrano[4,3-b]indoles and 2,3-dihydrofurans. The radical–radical cross-coupling of the radical species generated by anodic oxidation combined with the cathodic generation of the base from O2 allows for mild reaction conditions for the synthesis of structurally complex heterocycles.

Palladium-Catalyzed C–S Bond Formation of Stable Enamines with Arene/Alkanethiols: Highly Regioselective Synthesis of β-Amino Sulfides

A direct and regiocontrolled thiolation method to access β-amino sulfides through the palladium-catalyzed C(sp2)–H functionalization of stable enamines was described. The reaction was realized under mild conditions by adding an external phosphi

Palladium-catalyzed oxidative amination of activated olefins with N-alkyl anilines for synthesis of tertiary (E)-enamines

An efficient palladium-catalyzed oxidative amination of olefins with secondary anilines for the synthesis of tertiary (E)-enamines has been developed. Trimethylacetic acid (PivOH) played an important role in the reaction. This protocol tolerates a range o

Efficient synthesis of β-enaminoesters via highly stereoselective Reformatsky reaction with disubstituted formamides as novel electrophiles

An efficient synthesis of various β-enaminoesters has been achieved via Reformatsky reaction with disubstituted formamides as novel electrophiles. The exclusive β-enaminoester E-isomers were obtained in 60-72% yield.

A novel cycloaddition reaction of α-diazo-γ-amido ketones catalyzed by rhodium(II) acetate. Scope and mechanistic details of the process

α-Diazo ketones containing an amido group in the γ-position have been found to underdo a novel rhodium(II)-catalyzed cycloaddition reaction. Intramolecular cyclization of the keto carbenoid onto the oxygen atom of the amide group generates a carbonyl ylide dipole as a transient species. This highly stabilized dipole does not readily undergo 1,3-dipolar cycloaddition but ruther transfers a proton to produce a cyclic ketene N,O-acetal. The ketene acetale is unstable to moisture and upon standing is readily hydrolyzed to a γ-keto-δ-lactone and an amine. In the absence of any significant amount of water, the ketene N,O-acetal undergoes conjugate addition with the activated ?-bond of the dipolarophile to give a zwitterion intermediate. The anionic portion of the zwitterion adds to the neighboring carbonyl group. This is followed by epoxide ring formation with charge dissipation leading to an amido-substituted spiro cyclopentenyl epoxide. In certain cases a hydroxyl lactone was also isolated and its formation can be attributed to the competitive hydrolysis of the zwitterionic intermediate. The Rh(II)-catalyzed reaction of the diazo ketoamide derived from N-benzylpiperidone with DMAD afforded two different types of cyloadducts. In addition to the spiro cyclopentenyl epoxide, a product derived from trapping of the carbonyl ylide dipole was also obtained, thereby providing additional support for the proposed mechanism.

Palladium-Assisted Functionalization of Olefins: A New Amination of Electron-Deficient Olefins

Palladium chloride catalyzed the reaction of substituted anilines with methyl vinyl ketone, methyl acrylate, and acrylonitrile to produce vinylogous arylamino ketones, esters, and nitriles.N-Methylaniline gave the highest yields.Aniline and benzylamine fa