5834-42-4

Upstream product

• 1889-77-6 2-bromo-1-(4-methoxy-phenyl)-2-phenyl-ethanone 
• 62-53-3 aniline 
• 6338-31-4 2-(4-methoxyphenyl)-1-phenyl-2-(phenylamino)ethan-1-one 
• 18820-82-1 Pyridine hydrobromide 
• 542-11-0 aniline hydrobromide 
• 66107-29-7 4-methoxyphenyl triflate 
• 143360-89-8 o-(phenylethynyl)trifluoroacetanilide 
• 459-64-3 4-methoxybenzenediazonium tetrafluoroborate 
• 528836-77-3 2-isothiocyanato-1-(2-phenyl-1-ethynyl)benzene 
• 623-12-1 4-chloromethoxybenzene 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 143321-89-5 2,2,2-trifluoro-N-(2-iodophenyl)acetamide 
• 536-74-3 phenylacetylene 
• 948-65-2 2-phenyl-indole 

Downstream Products

• 112724-00-2 1-methyl-2-phenyl-3-(4-methoxyphenyl)-1H-indole 
• 36305-84-7 N-[2-(p-methoxybenzoyl)phenyl]benzamide 
• 112724-01-3 1-Ethyl-3-(4-methoxy-phenyl)-2-phenyl-1H-indole 
• 6916-99-0 4-(1-methyl-2-phenyl-1H-indol-3-yl)phenol 
• 6910-83-4 3-(4-Hydroxyphenyl)-2-phenylindole 
• 112724-09-1 Acetic acid 4-(1-ethyl-2-phenyl-1H-indol-3-yl)-phenyl ester 

Relevant academic research and scientific papers

Sequential Sonogashira/intramolecular aminopalladation/cross-coupling ofortho-ethynyl-anilines catalyzed by a single palladium source: rapid access to 2,3-diarylindoles

We have developed a practical and efficient one-pot protocol for the synthesis of 2,3-diarylindolesviaPd-catalyzed bis-arylative cyclization of variouso-ethynylanilines with aryl iodides. Mechanism studies showed that a Pd-catalyzed Sonogashira reaction took place firstly, giving an internal alkyne intermediate, which subsequently underwent intramolecular aminopalladation/cross-coupling to give access to 2,3-diarylindoles. The present methodology exhibits a broad substrate scope, producing various 2,3-diaryl indoles bearing two different aryl groups.

Direct C3-Selective Arylation of N-Unsubstituted Indoles with Aryl Chlorides, Triflates, and Nonaflates Using a Palladium-Dihydroxyterphenylphosphine Catalyst

A palladium-dihydroxyterphenylphosphine (DHTP) catalyst was successfully applied to the direct C3-arylation of N-unsubstituted indoles with aryl chlorides, triflates, and nonaflates. This catalyst showed C3-selectivity, whereas catalysts with other structurally related ligands exhibited N1-selectivity. Complex formation between the lithium salts of the ligand and the indole is assumed to accelerate the arylation at the C3 position. Reactions using 3-alkylindoles afforded 3,3-disubstituted indolenines, which can be further converted to the corresponding indoline derivatives.

Arylation synthesis method for novel five-membered aromatic heterocycle and aromatic-ring five-membered aromatic heterocycle

The invention belongs to the technical field of organic synthesis and in particular relates to an arylation synthesis method for a five-membered aromatic heterocycle or an aromatic-ring five-memberedaromatic heterocycle under the participation of an arylhydrazine derivative serving as a novel arylation reagent. The method comprises the steps: adding a raw material and aroyl hydrazine into a reactor, and carrying out a reaction at 60-100 DEG C for 8-24h under the condition that an oxidant and a transition metal catalyst are added; after the reaction is ended, carrying out suction filtration, extracting a filtrate by using ethyl acetate, carrying out drying to obtain a crude product of a target compound, and carrying out column chromatography on silica gel to obtain a pure product of the target compound. The arylation synthesis method for the five-membered aromatic heterocycle or the aromatic-ring five-membered aromatic heterocycle is scientific and reasonable and has the advantages such as simplicity and convenience in operation, relatively high yield and simplicity in amplification and purification.

Palladium-Catalyzed Synthesis of Indoles and Isoquinolines with in Situ Generated Phosphinimine

A palladium-catalyzed synthesis of polysubstituted indoles and isoquinolines through the coupling of aryl bromides with 2-alkynyl arylazides or 2-alkynyl benzylazides has been developed. This method provides straightforward access to indoles and isoquinolines with high efficiency and excellent functional group compatibility. In this transformation, the iminophosphorane in situ generated from azides is served as the nucleophile that attacks the alkyne moiety in the cyclization process.

Transition-metal-free, visible-light-mediated cyclization of: O -azidoarylalkynes with aryl diazonium salts

Visible light along with 3 mol% eosin Y catalyzes the cyclization reaction of o-azidoarylalkynes with aryl diazonium salts by a photoredox process. We have investigated the scope of the reaction for several aryl diazonium salts and o-azidoarylalkynes. The general and easy procedure provides a transition-metal-free alternative for the formation of unsymmetrical 2,3-diaryl-substitued indoles.

Transition-metal-free, visible-light induced cyclization of arylsulfonyl chlorides with o-azidoarylalkynes: a regiospecific route to unsymmetrical 2,3-disubstituted indoles

A visible-light-catalyzed synthesis of unsymmetrical 2,3-diaryl-substituted indoles from arylsulfonyl chlorides and o-azidoarylalkynes at room temperature has been discovered. This transformation exhibits excellent substrate scope and functional group tolerance. The use of inexpensive eosin Y as the catalyst with easy operation makes this protocol very practical.

Method for preparing indole derivative by reaction between nitrone derivative and symmetric alkyne

The invention relates to a method for preparing an indole derivative by a reaction between a nitrone derivative and symmetric alkyne and particularly relates to a novel method for preparing a 2,3-asymmetric indole derivative by a reaction between a nitron

A synthetic 2,3-diarylindole induces cell death via apoptosis and autophagy in A549 lung cancer cells

A series of 2,3-diarylindoles were synthesized via the Larock heteroannulation, and evaluated for their anticancer activity against A549 lung cancer cells. The most potent compound, PCNT13 with IC50 = 5.17 μM, caused the induction of two modes of programmed cell death, apoptosis and autophagy.

Rhodium-Catalyzed C-H Annulation of Nitrones with Alkynes: A Regiospecific Route to Unsymmetrical 2,3-Diaryl-Substituted Indoles

The direct C-H annulation of anilines or related compounds with internal alkynes provides straightforward access to 2,3-disubstituted indole products. However, this transformation proceeds with poor regioselectivity in the synthesis of unsymmetrically 2,3-diaryl substituted indoles. Herein, we report the rhodium(III)-catalyzed C-H annulation of nitrones with symmetrical diaryl alkynes as an alternative method to prepare 2,3-diaryl-substituted N-unprotected indoles with two different aryl groups. One of the aryl substituents is derived from N?C-aryl ring of the nitrone and the other from the alkyne substrate, thus providing the indole products with exclusive regioselectivity.

Aqueous Titanium Trichloride Promoted Reductive Cyclization of o-Nitrostyrenes to Indoles: Development and Application to the Synthesis of Rizatriptan and Aspidospermidine

Treatment of o-nitrostyrenes with aqueous TiCl3 solution at room temperature afforded indoles through a formal reductive C(sp2)-H amination process. A range of functions such as halides (Cl, Br), carbonyl (ester, carbamate), cyano, hydroxy, and amino groups were tolerated. From β,β-disubstituted o-nitrostyrenes, 2,3-disubstituted indoles were formed by a domino reduction/cyclization/migration process. Mild conditions, simple experimental procedure, ready accessibility of the starting materials and good to excellent yields characterize the present transformation. The methodology was used as a key step in a concise synthesis of rizatriptan and a formal total synthesis of aspidospermidine. Mild and efficient treatment of o-nitrostyrenes with aqueous TiCl3 solution at room temperature afforded indoles through a formal reductive C(sp2)-Hamination process. A concise synthesis of a marketed drug (rizatriptan) and a formal total synthesis of aspidospermidine featuring this novel N-heterocyclization process are reported.