76609-18-2

Upstream product

• 26031-63-0 1-(2-(4-fluorophenyl)-2-oxoethyl)pyridine-1-ium bromide 
• 106-49-0 p-toluidine 
• 403-29-2 2-bromo-4'-fluoroacetophenone 
• 583-68-6 2-bromo-p-toluidine 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 403-43-0 4-fluorobenzoyl chloride 
• 352-34-1 4-fluoro-1-iodobenzene 
• 614-96-0 5-methyl-1H-indole 
• 556053-57-7 trans-3-(4-fluorophenyl)oxirane-2-carbonitrile 
• 459-57-4 4-fluorobenzaldehyde 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 556053-57-7 3-(4-fluorophenyl)-2-cyanooxirane 
• 539-44-6 N-4-methylphenylhydrazine 
• 399-05-3 4-fluoro-N-(4-methylphenyl)benzamide 

Relevant academic research and scientific papers

α-Imino Iridium Carbenes from Imidoyl Sulfoxonium Ylides: Application in the One-Step Synthesis of Indoles

Imidoyl sulfoxonium ylides are presented for the first time as potential precursors to generate α-imino metal-carbene intermediates and applied in direct C-H functionalization reactions catalyzed by [Ir(cod)Cl]2 (4 mol %) to provide 2-substituted indoles (up to 70% yield) in just one step. This class of sulfur ylide is successfully obtained from imidoyl chloride and dimethylsulfoxonium methylide (23 new examples in 45-85% yield) or by imino group formation from the corresponding β-keto sulfoxonium ylides and anilines in the presence of TiCl4 as a Lewis acid (9 examples in 33-94% yield).

A micellar catalysis strategy applied to the Pd-catalyzed C-H arylation of indoles in water

The selective control over multiple competing C-H sites would enable straightforward access to functionalized indoles. In this context, we report here a modular and selective C-H arylation of indoles following the micellar catalysis approach using the third generation "designer" surfactant SPGS-550-M in the presence of 1 mol% of [(cinnamyl)PdCl]2 under mild conditions. Thus, access to high value C-arylated (C-3 and C-2) indoles was achieved fulfilling the "triple bottom line philosophy" of green chemistry. The nature of the phosphine ligand was found to be critical for achieving site-selectivity, DPPF and DPPP being the most effective in promoting the arylation at C3-H and C2-H, respectively. The reaction is scalable and offers high chemo- (C vs. N) and regio-selectivity (C-3 vs. C-2) with a wide range of functional group tolerance. The surfactant aqueous solution can be recycled and reused without compromising on product yields.

2-Phenylindole derivatives as anticancer agents: synthesis and screening against murine melanoma, human lung and breast cancer cell lines

Indole derivatives have attractive anticancer properties and may be a future hope for better anticancer drug(s) of low toxicity and high potency. In this paper, syntheses of 2-phenylindole derivatives have been described via Fischer indole synthesis through a one-pot solvent-free method. The synthesized compounds were screened for anticancer potential in vitro against murine melanoma (B16F10), human lung cancer (A549), and human breast cancer (MDA-MB-231) cell lines. The results highlighted that 2-phenylindole derivatives are also promising anticancer agents in case of melanoma and lung cancer along with the breast cancer. Molecular docking analyses with possible targets for melanoma (NEDD4-1) and lung cancer (EGFR) were also performed to understand specific interactions of 2-phenylindole derivatives with the amino acid residues of the receptors.

Preparation method of indole compounds

The invention provides a preparation method of indole compounds. 2-cyanoethylene oxide compounds and arylamine react under the catalysis effect of lewis acid (boron trifluoride diethyl etherate or aluminum trichloride) to obtain corresponding indole compo

Oxygenophilic Lewis Acid Promoted Synthesis of 2-Arylindoles from Anilines and Cyanoepoxides in Alcohol

A convenient synthetic method to indoles from anilines and cyanoepoxides was developed under the catalysis of BF3·OEt2 or AlCl3 in alcohols. The reaction involves a tandem reaction of the regiospecific ring-opening of cyanoepoxides with anilines, elimination of cyanide, intramolecular aromatic electrophilic substitution, and water elimination. The Lewis acid generated protic acid is an efficient catalyst. The method features readily accessible starting materials, wide substrate scope, transition-metal-free environment, and regiospecificity in the ring-opening of cyanoepoxides.

Palladium-Catalyzed C2?H Arylation of Unprotected (N?H)-Indoles “On Water” Using Primary Diamantyl Phosphine Oxides as a Class of Primary Phosphine Oxide Ligands

We present the Pd-catalyzed arylation of (N?H)-indoles with functionalized haloarenes “on water” using hitherto untested primary diamantyl phosphine oxides (PPO) as ligands. Remarkable C2?H arylation selectivity was achieved by employing functionalized iodoarenes and N-unprotected indoles. We provide evidence that the in situ generated oxide of (9-hydroxydiamant-4-yl)phosphine L1 is key for the reaction efficiency by comparing a set of diamantane-based compounds structurally related to L1. Our results demonstrate the power of the new PPO ligands for the C?H functionalization of unprotected (N?H)-heterocycles.

Synthesis of Indoles and Pyrroles Utilizing Iridium Carbenes Generated from Sulfoxonium Ylides

Metal carbenes can undergo a myriad of synthetic transformations. Sulfur ylides are potential safe precursors of metal carbenes. Herein, we report cascade reactions that involve carbenoids derived from sulfoxonium ylides for the efficient and regioselective synthesis of indoles and pyrroles. The tandem action of iridium and Br?nsted acid catalysts enables rapid assembly of the heterocycles from unmodified anilines or readily accessible enamines under microwave irradiation. The key mechanistic steps are the catalytic transformation of the sulfoxonium ylide into an iridium–carbene complex, followed by N?H or C?H functionalization of an aniline or enamine, respectively, and a final acid-catalyzed cyclization. The present method was successfully applied to the synthesis of the densely functionalized pyrrole subunit of atorvastatin.

Well-defined NHC-Pd complex-mediated intermolecular direct annulations for synthesis of functionalized indoles (NHC = N-hetero-cyclic carbene)

As alternatives to the common tertiary phosphine/Pd systems, well-defined N-heterocyclic carbene-Pd complexes have been proven to be highly efficient precatalysts for intermolecular direct annalution of o-haloanilines and ketones at lower catalyst loadings. A highly efficient and practical protocol for synthesis of functionalized indoles was developed using (IPr)Pd(acac)Cl as catalyst. Both o-bromoanilines and o-chloroanilines gave rise to efficient coupling under the reaction conditions. Related to acyclic ones, cyclic ketones coupled more effectively with o-haloanilines. With [Pd(IPr)2] as catalyst, the base-sensitive groups including OH and CO2H groups could be tolerated. Copyright

Synthesis of Some New Fluorinated Indoles and Benzindoles through Pyridinium Ylids

Three fluorinated phenacylpyridinium bromides (1a-c) have been prepared and reacted with various anilines to obtain 2-(fluoroaryl)indoles (3a-r).A similar reaction of 1 with 1- and 2-naphthylamines furnishes 2-(fluoroaryl)-1H-benzindoles (4a-c) and 2-(fluoroaryl)-3H-benzindoles (5a-c), respectively.All the products have been identified on the basis of elemental analyses, IR, PMR and 19F NMR spectra.