35577-89-0

Usage

Structure

A tosyl derivative of indole, a bicyclic compound consisting of a benzene ring fused to a pyrrole ring, with a tosyl group (a sulfonamide group) attached to the nitrogen atom of the pyrrole ring.

Uses

A key intermediate in the synthesis of various pharmaceutical compounds, with potential applications in the development of new drugs for the treatment of viral and malarial infections. It is also used in the production of dyes and pigments, as well as in organic synthesis.

Properties

Exhibits anti-viral and anti-malarial properties.

Upstream product

• 13754-86-4 1,5,6,7-tetrahydro-indol-4-one 
• 104-15-4 toluene-4-sulfonic acid 
• 127-65-1 chloroamine-T 
• 98-59-9 p-toluenesulfonyl chloride 
• 107-20-0 2-chloroethanal 
• 504-02-9 1,3-cylohexanedione 
• 76988-93-7 C₂₁H₂₈N₂O₄S 

Downstream Products

• 107170-62-7 cis-4-(ethoxycarbonylmethylidene)-1-(p-toluenesulfonyl)-4,5,6,7-tetrahydroindole 
• 107170-61-6 trans-4-(ethoxycarbonylmethylidene)-1-(p-toluenesulfonyl)-4,5,6,7-tetrahydroindole 
• 106154-13-6 1-[(4-methylbenzene)sulfonyl]-4-[(trimethylsilyl)oxy]-4,5,6,7-tetrahydro-1H-indole-4-carbonitrile 
• 113484-99-4 4-Methanesulfonylmethyl-1-(toluene-4-sulfonyl)-4,5,6,7-tetrahydro-1H-indol-4-ol 
• 107170-55-8 [1-(Toluene-4-sulfonyl)-1,5,6,7-tetrahydro-indol-(4Z)-ylidene]-acetonitrile 
• 107196-76-9 [1-(Toluene-4-sulfonyl)-1,5,6,7-tetrahydro-indol-(4E)-ylidene]-acetonitrile 
• 106507-71-5 4-bis-(phenylthio)methyl-4-hydroxy-1-(p-toluenesulfonyl)-4,5,6,7-tetrahydroindole 
• 113484-98-3 4-Benzenesulfonylmethyl-1-(toluene-4-sulfonyl)-4,5,6,7-tetrahydro-1H-indol-4-ol 
• 107170-65-0 4-(3-methylbut-2-enylidene)-1-(p-toluenesulfonyl)-4,5,6,7-tetrahydroindole 
• 95969-07-6 5-chloro-4-oxo-N-(p-toluenesulfonyl)-4,5,6,7-tetrahydroindole 
• 76989-06-5 5-bromo-4-oxo-N-(p-toluenesulfonyl)-4,5,6,7-tetrahydroindole 
• 95969-12-3 2-chloro-4-oxo-N-(p-toluenesulfonyl)-4,5,6,7-tetrahydroindole 
• 95969-11-2 5,5-dibromo-4-oxo-N-(p-toluenesulfonyl)-4,5,6,7-tetrahydroindole 
• 81038-34-8 1-(p-toluenesulphonyl)-4-hydroxyindole 

Relevant academic research and scientific papers

Synthesis of Pyrroles via Consecutive 6π-Electrocyclization/Ring-Contraction of Sulfilimines

We present a modular, synthetic entry to polysubstituted pyrroles employing readily available 2,5-dihydrothiophenes. Ring-opening of the heterocycle provides access to a panel of 1,3-dienes which undergo pyrrole formation in the presence of inexpensive chloramine-T trihydrate. The transformation is conducted in an open flask and proceeds at ambient temperatures (23 °C) in nondry solvents. A careful adjustment of the electronics and sterics of the 1,3-diene precursor allows for the isolation of key intermediates. DFT studies identified a reaction mechanism that features a 6π-electrocyclization of a sulfilimine intermediate followed by spontaneous ring-contraction to reveal the pyrrole skeleton.

Synthesis and Spectroscopic Properties of 1,2,3-Triazole BOPAHY Dyes and Their Water-Soluble Triazolium Salts

Water-soluble BOPAHY fluorophores have not yet been reported. The potential of 1,2,3-triazolium salts for the formation of water-soluble chromophores is explored. 1,2,3-Triazole-substituted pyrroles were synthesized in a metal-free pathway and alkylated t

PYRANOPYRAZOLE AND PYRAZOLOPYRIDINE IMMUNOMODULATORS FOR TREATMENT OF AUTOIMMUNE DISEASES

Pyranoyrazoles and pyrazolopyridines of formula I or formula II are disclosed: (I), (II) These compounds inhibit Coagulation Factor Xlla in the presence of thrombin and other coagulation factors. They are useful to treat autoimmune diseases.

AMINOACYLINDAZOLE IMMUNOMODULATORS FOR TREATMENT OF AUTOIMMUNE DISEASES

2-Acylindazole compounds of formula I or formula II are disclosed. These compounds inhibit Coagulation Factor XIIa. They are useful to treat autoimmune diseases.

Synthesis and binding assays of novel 3,3-dimethylpiperidine derivatives with various lipophilicities as σ1 receptor ligands

Starting from two carbocyclic analogs, a series of 3,3-dimethylpiperidine derivatives was prepared and tested in radioligand binding assays at σ1 and σ2 receptors, and at Δ8-Δ7 sterol isomerase (SI) site. The novel compounds mostly bear heterocyclic rings or bicyclic nucleus of differing lipophilicities. Compounds 18a and 19a,b demonstrated the highest σ1 affinity (Ki = 0.14-0.38 nM) with a good selectivity versus σ2 binding. Among them, 18a had the lowest C log D value (3.01) and only 19b was selective versus SI too. Generally, it was observed that more planar and hydrophilic heteronuclei conferred a decrease in affinity for both σ receptor subtypes.

Intramolecular palladium-catalyzed alkane C-H arylation from aryl chlorides

The first examples of efficient and general palladium-catalyzed intramolecular C(sp3)-H arylation of (hetero)aryl chlorides, giving rise to a variety of valuable cyclobutarenes, indanes, indolines, dihydrobenzofurans, and indanones, are described. The use of aryl and heteroaryl chlorides significantly improves the scope of C(sp3)-H arylation by facilitating the preparation of reaction substrates. Careful optimization studies have shown that the palladium ligand and the base/solvent combination are crucial to obtaining the desired class of product in high yields. Overall, three sets of reaction conditions employing PtBu3, PCyp3, or PCy3 as the palladium ligand and K 2CO3/DMF or Cs2CO3/pivalic acid/mesitylene as the base/solvent combination allowed five different classes of products to be accessed using this methodology. In total, more than 40 examples of C-H arylation have been performed successfully. When several types of C(sp3)-H bond were present in the substrate, the arylation was found to occur regioselectively at primary C-H bonds vs secondary or tertiary positions. In addition, in the presence of several primary C-H bonds, selectivity trends correlate with the size of the palladacyclic intermediate, with five-membered rings being favored over six- and seven-membered rings. Regio- and diastereoselectivity issues were studied computationally in the prototypal case of indane formation. DFT(B3PW91) calculations demonstrated that C-H activation is the rate-determining step and that the creation of a C-H agostic interaction, increasing the acidity of a geminal C-H bond, is a critical factor for the regiochemistry control.

Synthesis of a 1,3,4,5-tetrahydrobenzindole β-ketoester

Pd(OAc)2-catalyzed decomposition of ethyl 2-diazo-4-(4-indolyl)-3- oxobutanoate leads to a tricyclic tetrahydrobenzindole compound formed by a formal C-H insertion reaction. This tricyclic indole rearranges to a novel and thermodynamically more stable nap

4-aryl substituted indolinones

The present invention relates to 4-arylindolinones, as well as pharmaceutical compositions thereof, capable of modulating protein kinase signal transduction in order to regulate, modulate and/or inhibit abnormal cell proliferation. The present invention also relates to methods for treating protein kinase related disorders.

Short step synthesis of 4-substituted indoles using palladium-catalyzed C-C bond forming reaction

Enol triflate of N-tosyl-4-oxo-tetrahydroindole (2) was a good precursor for a synthesis of 4-substituted indoles. Various functional groups were introduced to form corresponding indoles using palladium-catalyzed carbonylation and a cross-coupling reaction followed by dehydrogenation by palladium on charcoal.

SELECTIVE CLEAVAGE OF UNSYMMETRICAL 2,2-SPIRO-1,3-DIOXOLANES. II. CLEAVAGE OF KETAL RING Of 5'-BROMO-6',7'-DIHYDRO-4-ISOPROPYLAMINOMETHYL-1'-p-TOLUENESULFONYL-SPIRO AND ITS ANALOGS

The bromodioxolane and its analogs (1-5) were treated with organic base (DBU, DBN, or morpholine), acid (p-toluenesulfonic acid or Lewis acid), or Lewis acid/tertiary amine, and yielded 4-alkoxyindoles (6-17).Reaction of 1 with organic base gave two isome