179487-70-8

Upstream product

• 120-72-9 indole 
• 17763-70-1 methyl 2-(trifluoromethylsulfonyloxy)benzoate 
• 610-94-6 2-bromobenzoic acid methyl ester 
• 610-97-9 o-iodo-methyl-benzoic acid 
• 88-67-5 2-Iodobenzoic acid 
• 25660-62-2 2-(1H-indol-1-yl)benzoic acid 
• 74-88-4 methyl iodide 

Downstream Products

• 25660-62-2 2-(1H-indol-1-yl)benzoic acid 
• 1146543-37-4 1-[2-(2,2-dibromo-vinyl)-phenyl]-1H-indole 
• 179487-71-9 2-indolylbenzyl alcohol 

Relevant academic research and scientific papers

Synthesis of Axially Chiral Olefin-Oxazoline Ligands via Pd-Catalyzed Multiple C-H Functionalization

We report herein the Pd-catalyzed oxazoline-directed C-H olefination of the N-arylindole skeleton, affording two diastereomers of axially chiral olefin-oxazoline ligands in a one-step procedure. Modifications at the 3- and 3′-positions were facilely achieved via electrophilic substitution of the indole fragment and subsequent oxazoline-directed C-H amidation or olefination of the arene fragment.

Palladium-catalyzed intramolecular C–H acylation of indoles with thioester

A palladium-catalyzed intramolecular C–H acylation of indole with thioester is described, providing a direct and effective approach for the synthesis of the biologically active indole-indolone scaffolds. The method obviates the need for the prefunctionalized starting materials including organometallic reagents, alkyl halides, and NHP esters in previous metal-catalyzed cross-coupling reaction with thioester. Substrates bearing sensitive halo groups are compatible in the reaction, leaving a functional handle for further structural elaborations.

Isocyanide-Induced Activation of Copper Sulfate: Direct Access to Functionalized Heteroarene Sulfonic Esters

A novel and direct approach to alkyl/aryl heteroarene sulfonic esters using copper sulfate as the environmentally benign inorganic sulfonation reagent was first realized with the aid of isocyanide. A variety of heterocycles reacted to afford the corresponding sulfonic esters through C?H functionalization. In this transformation, the otherwise inert copper sulfate was unusually activated by an isocyanide and employed as the source of the sulfonic substituents in an unprecedented fashion. The findings suggest that an appropriate activator may liberate the chemical activities of some relatively inert inorganic salts for organic synthesis.

Synthesis of pyrrolo-/indolo[1,2-a ]quinolines and naphtho[2,1- b ]thiophenes from gem -dibromovinyls and sulphonamides

A highly efficient and simple route for the synthesis of pyrrolo-/indolo[1,2-a]quinolines and naphtho[2,1-b]thiophenes from gem-dibromovinyls and sulphonamides is reported. The noteworthy feature of this report is that the methodology involves a two-step protocol to synthesize tri- and tetracyclic heterocycles in a one-pot fashion through the Cu(I)-catalyzed formation of ynamide followed by a Ag(I)-assisted intramolecular hydroarylation. The photophysical properties of representative examples of pyrrolo- and indolo[1,2-a]quinolines in solid and solution states have also been studied.

Active manganese dioxide promoted cyclization of ortho-(1H-pyrrol-1-yl)aryl and heteroaryl carboxylic acids to 5H-pyrrolo[1,2-a][3,1]benzoxazin-5-one derivatives

The hitherto unknown lactone 5H-pyrrolo[1,2-a][3,1]benzoxazin-5-one and six of its substituted derivatives have been prepared by active manganese dioxide promoted oxidative cyclization of the corresponding 2-(1H-pyrrol-1-yl)benzoic acids, under mild conditions, in moderate yields. The method was successfully extended to the cyclization of some ortho-(1H-pyrrol-1-yl)heteroaryl carboxylic acids and 2-(1H-indol-1-yl)benzoic acids.

An expedient synthesis of indolo[1,2-a]quinolines via Mn(OAc)3-mediated oxidative free radical cyclization and NaI/O2-assisted dealkoxycarbonylation/ aerobic oxidation cascade

An expedient synthetic procedure of indolo[1,2-a]quinolines was developed using a sequential Cu-mediated N-arylation of indole, Mn(OAc) 3-mediated oxidative free radical cyclization, and NaI/O 2-assisted concomitant dealkoxycarbonylation/aerobic oxidation. The last step was replaced by a palladium-catalyzed decarboxylation/elimination protocol for the allyl ester derivatives.

Isoindolo[2,1-a]indol-6-one-a new pyrolytic synthesis and some unexpected chemical properties

Isoindolo[2,1-a]indol-6-one 1 is formed by a sigmatropic shift-elimination-cyclisation cascade by flash vacuum pyrolysis (FVP) of methyl 2-(indol-1-yl)benzoate 7 at 950 °C. The dihydro compound 16 is easily obtained by catalytic reduction of 1, but the reaction is very sensitive to steric effects at the 11-position. Attempted ring-opening of 1 in basic methanol provides an equilibrium of isoindolo[2,1-a]indol-6-one 1 and the ester 19. Lithium aluminium hydride reduction of 1 provides the alcohol 22 which can be dehydrated to a mixture of 23 and 24 by FVP at 800-950 °C.

Method for arylating aza-heterocycles with activated aromatic compounds in the presence of caesium carbonate

The invention concerns a process for the preparation of N-aryl-aza-heterocycles of the general formula I by reaction of aza-heterocycles with activated aryl halides with use of caesium carbonate without addition of further catalysts at room temperature.

Efficient palladium-catalyzed N-arylation of indoles

(Matrix presented) The N-arylation of indoles, including a variety of substituted ones, has been carried out using bulky, electron-rich phosphines as the supporting ligand in combination with Pd2(dba)3. Using this catalyst system, th

Anti-inflammatory benzoic acid derivatives

Novel benzoic acid derivatives have the formula: STR1 wherein --X-- represents C1 to C6 alkylene, C2 to C6 alkenylene or a divalent moiety having the structure --(CH2)m --Z-- in which m is an integer from 0 to 3 and Z represents --O--, --S-- or --NH--; --Y-- represents a direct bond, C1 to C6 alkylene, C2 to C6 alkenylene or a divalent moiety having the structure --(CH2)m --Z--(CH2)n in which m and n are each, independently, an integer from 0 to 3 and --Z-- represents --O--, --S-- or --NH--; R represents a 5- or 6-membered carbocyclic or heterocyclic ring or a carbocyclic or heterocyclic fused ring system containing up to 10 members in the ring, which carbocyclic, heterocyclic or fused ring system may be saturated or unsaturated and may contain up to two substituents selected from lower alkyl, methoxy, halo and trifluoromethyl; and R1 and R2 are each, independently, selected from hydrogen, lower alkyl, methoxy, halo and trifluoromethyl. The benzoic acid derivates are useful as anti-inflammatory agents.