88207-52-7

Usage

Class of compound

Heterocyclic (indoles)

Structural features

Methylsulfonyl group attached to the first carbon of the indole ring, phenyl group attached to the second carbon

Potential uses

Biological activity, drug discovery and development

Importance

Versatile compound with potential applications in the pharmaceutical industry

Upstream product

• 536-74-3 phenylacetylene 
• 125345-25-7 N-(2-phenylethynylphenyl)methanesulfonamide 
• 98-88-4 benzoyl chloride 
• 62-53-3 aniline 
• 100-42-5 styrene 
• 1197-22-4 N-phenylmethanesulfonamide 
• 70390-93-1 1-(methylsulfonyl)indole 
• 71-43-2 benzene 
• 120-72-9 indole 
• 100-52-7 benzaldehyde 
• 27652-35-3 (E)-2-styrylaniline 
• 615-36-1 2-bromoaniline 
• 116547-92-3 N-(2-iodophenyl)methanesulfonamide 
• 13141-38-3 2-phenylethynylaniline 

Downstream Products

• 1220995-75-4 3-chloro-N-methanesulfonyl-2-phenylindole 

Relevant academic research and scientific papers

Catalytic Enantioselective Aminopalladation–Heck Cascade

Domino processes initiated by intramolecular nucleopalladation of alkynes have been developed into powerful synthetic tools for the synthesis of functionalized heterocycles. However, a catalytic enantioselective version of this class of reactions remains

DMSO/SOCl2-mediated C(sp2)-H amination: Switchable synthesis of 3-unsubstituted indole and 3-methylthioindole derivatives

The reaction of 2-alkenylanilines with SOCl2 in DMSO was found to selectively afford 3-unsubstituted indoles and 3-methylthioindoles. This switchable approach was found to be temperature-dependent: at room temperature, the reaction afforded 3-unsubstituted indoles through intramolecular cyclization and elimination; while at higher temperature, the reaction gave 3-methylthioindoles via further electrophilic methylthiolation.

Synthetic method of indole derivative

The invention discloses a synthesis method of an indole derivative, which comprises the following steps: dissolving a raw material o-vinylaniline derivative II in dimethyl sulfoxide, dropwise adding thionyl chloride, and reacting to obtain an indole deriv

Tandem Phospha-Michael Addition/N-Acylation/ Intramolecular Wittig Reaction of aza-o-Quinone Methides: Approaches to 2,3-Disubstituted Indoles

A tandem phospha-Michael addition/N-acylation/intramolecular Wittig reaction of in situ formed aza-o-QMs is disclosed. This approach features high functional group tolerance and provides a convenient and practical access to biologically significant indole derivatives (37 examples, up to 91% yield) under mild reaction conditions. (Figure presented.).

An efficient synthesis of indoles via a CuMgAl-LDH-catalyzed cyclization of 2-alkynylsulfonanilides

A highly efficient method for the synthesis of indoles has been successfully developed via a CuMgAl-LDH-catalyzed intramolecular annulation reaction of 2-alkynylsulfonanilides. This CuMgAl-LDH catalyst features facile preparation, recovery, and reuse at l

Simultaneous functionalization and cyclization of 2-ethynylaniline derivatives to indoles

Two different kind of sequential cyclization-functionalization are developed. Namely, cyclization-chlorination of 2-ethynylaniline derivatives using CuCl2 gave 3-chloro- and 3,5-dichloroindole derivatives. The plausible mechanism for this react

Palladium-Catalyzed Regioselective Synthesis of 3-Arylindoles from N-Ts-Anilines and Styrenes

A Pd-catalyzed intermolecular oxidative annulation between N-Ts-anilines and styrenes was developed. This method offers a straightforward and robust approach to a wide range of 3-arylindoles using readily available starting materials with good functional-group tolerance and high regioselectivity and efficiency. Further elaboration of the products obtained from this process provided access to highly functionalized and structurally diverse indoles, for example, 3-(indol-3-yl)carbazoles, 1,9-dihydropyrrolo-[2,3-b]carbazoles, and 3′-aryl-3,5′-biindoles.

Synthesis of Benzofurans and Indoles from Terminal Alkynes and Iodoaromatics Catalyzed by Recyclable Palladium Nanoparticles Immobilized on Siliceous Mesocellular Foam

Herein, we report on the utilization of a heterogeneous catalyst, consisting of Pd nanoparticles supported on a siliceous mesocellular foam (Pd0-AmP-MCF), for the synthesis of heterocycles. Reaction of o-iodophenols and protected o-iodoanilines with acetylenes in the presence of a Pd nanocatalyst produced 2-substituted benzofurans and indoles, respectively. In general, the catalytic protocol afforded the desired products in good to excellent yields under mild reaction conditions without the addition of ligands. Moreover, the structure of the reported Pd nanocatalyst was further elucidated with extended X-ray absorption fine-structure spectroscopy, and it was proven that the catalyst could be recycled multiple times without significant loss of activity.

Palladium-catalyzed regioselective C-2 arylation of 7-azaindoles, indoles, and pyrroles with arenes

A palladium-catalyzed regioselective C-2 arylation of 7-azaindoles, indoles, and pyrroles with arenes has been developed. This study unveils that a critical substrate dependent acid concentration is essential for achieving exclusive C-2 selectivity as wel

A concise approach to indoles via oxidative C-H amination of 2-alkenylanilines using dioxygen as the sole oxidant

A novel synthetic method to prepare indole derivatives from N-Ts-2-alkenylanilines has been achieved. This reaction is through an oxidative intramolecular C-H amination by using molecular oxygen as the sole oxidant. This protocol is operationally simple a