61327-27-3

Upstream product

• 54567-10-1 N-(2-benzoylphenyl)-formamide 
• 2787-08-8 N-methyl-2-styrylpyridinium iodide 
• 107125-70-2 lithium N-phenyl-N-methylcarbamate 
• 100-52-7 benzaldehyde 
• 119515-94-5 [2-(Methyl-propoxy-amino)-phenyl]-phenyl-methanol 
• 6120-94-1 N-methylanilinochlorophenylborane 
• 71492-76-7 N-allyl-N-methyl-2-bromoaniline 
• 119515-88-7 N-(2-bromophenyl)-N-methyl-O-propylhydroxylamine 
• 119515-87-6 o-bromo-N-methyl-N-allyloxyaniline 
• 100-61-8 N-methylaniline 
• 7755-70-6 2-(methylamino)benzaldehyde 
• 100-58-3 phenylmagnesium bromide 
• 3947-76-0 N-methylquinolinium iodide 
• 91-22-5 quinoline 

Downstream Products

• 81568-08-3 Benzoic acid [2-(benzoyl-methyl-amino)-phenyl]-phenyl-methyl ester 

Relevant academic research and scientific papers

Ru-Catalyzed Selective Catalytic Methylation and Methylenation Reaction Employing Methanol as the C1 Source

Methanol can be employed as a green and sustainable methylating agent to form C-C and C-N bonds via borrowing hydrogen (BH) methodology. Herein we explored the activity of the acridine-derived SNS-Ru pincer for the activation of methanol to apply it as a C1 building block in different reactions. Our catalytic system shows great success toward the β-C(sp3)-methylation reaction of 2-phenylethanols to provide good to excellent yields of the methylated products. We investigated the mechanistic details, kinetic progress, and temperature-dependent product distribution, which revealed the slow and steady generation of in situ formed aldehyde, is the key factor to get the higher yield of the β-methylated product. To establish the environmental benefit of this reaction, green chemistry metrics are calculated. Furthermore, dimerization of 2-naphthol via methylene linkage and formation of N-methylation of amine are also described in this study, which offers a wide range of substrate scope with a good to excellent yield.

Copper-Catalyzed (4+1) Cascade Annulation of Terminal Alkynes with 2-(Tosylmethyl)anilines: Synthesis of 2,3-Disubstituted Indoles

A novel strategy based on Cu-catalyzed (4+1) cascade annulation of terminal alkynes as one-carbon synthons with 2-(tosylmethyl)anilines has been developed for the expeditious synthesis of 2,3-disubstituted indoles, in which in situ generations of aza-o-quinone methides and alkynyl-copper(I) species are involved. This annulation provides an effective method for the assembly of synthetically and structurally interesting 2,3-disubstituted indoles.

An efficient iron-promoted synthesis of 6H-indolo[2,3- b] quinolines and neocryptolepine derivatives

A facile and practical method for the preparation of 6H-indolo[2,3-b]quinolines and neocryptolepines was developed under the promotion of the easily available ferric trichloride, affording the desired products with moderate to good yields.

Preparation of ortho-hydroxyalkylanilines as ortho-quinone methide imine precursors via an aminoborane complex

A general process for ortho-specific hydroxyalkylation of secondary anilines has been developed.N-Methylanilinochlorophenylboranes react readily with aryl aldehydes, and with α,β-unsaturated or saturated aliphatic aldehydes to give the corresponding ortho-hydroxyalkylanilines in good yield.Thermolysis of the latter generated the corresponding ortho-quinone methide imine, which can participate in an electrocyclic or intramolecular cycloaddition reaction to give various dihydro- and tetrahydroquinoline derivatives.Application of the method to the syntheses of 5-aza anal ogs of hexahydrocannabinol is demonstrated.Key words: quinone methide imine, ortho-hydroxyalkylaniline, azacannabinoids.

A SYNTHETIC EQUIVALENT FOR ORTHO-LITHIO-N-METHYLANILINE

o-Bromo-N-methyl-N-n-propoxyaniline undergoes halogen-metal exchange with butyllithium and the resulting lithio species reacts cleanly with a variety of electrophiles.The N-O bond of these products can be reduced with Raney nickel to afford ortho-substituted-N-methylanilines.

SELECTIVE REDUCTION OF KETONES WITH SODIUMBOROHYDRIDE-ACETIC ACID

Aliphatic ketones, and aromatic ketones having o-hydroxy or o-amino substituents are reduced rapidly to the alcohols by NaBH4 and acetic acid; other types of ketones react much more slowly.

Carbon Dioxide: A Reagent for the Simultaneous Protection of Nucleophilic Centres and the Activation of Alternative Locations to Electrophilic Attack. Prt III. A New Synthetic Method for the ortho-Substitution of N-Monoalkylanilines

N-Methyl- and N-ethyl-aniline are regiospecifically converted into a range of ortho-substituted derivatives, using carbon dioxide both for N-protection and as an intermediate carbanion stabilizing group, and t-butyllithium to lithiate the ortho-carbon atom.The rersulting lithium N-(ortho-substituted-phenyl)-N-methyl- and -N-ethylcarbamates undergo smooth acid-catalysed decarboxylation under mild conditions.No alpha-substituted products were detected.

Heterocyclic 8?-Systems, 15. Investigations on Indole 2,3-Oxides: Sythesis of 3-Hydroxyindoles via Intramolecular Wittig-Rearrangement of 1,2-Dihydro-4H-3,1-benzoxazines

Investigations to trap indole 2,3-oxides 11 by base catalyzed ring contraction of 4H-3,1-benzoxazines 3 led in the system KNH2/NH3 to 3-hydroxy-3H-indoles 7.The N-methylbenzoxazinium salts 15, obtained from 3 and FSO3CH3, yielded with ethoxide under kinet

Recyclization of 2-vinylpyridinium quaternary salts

It is shown that in the reaction of 2-vinylpyridinium quaternary salts with methylammonium sulfite under isomerization recyclization conditions a water molecule adds initially to the double bond of the vinyl substituents, after which the resulting carbino