153633-35-3

Usage

Class

pyrrole derivatives
Sulfonyl derivative of 1-phenyl-1H-pyrrole
4-methylphenyl group attached to sulfonyl moiety
Used in organic synthesis and pharmaceutical applications
Potential biological activities
Sulfonyl group imparts unique reactivity and functionality
Valuable building block in organic and medicinal chemistry.

Upstream product

• 39485-66-0 5-phenyl-2-(toluene-4-sulfonyl)-3,6-dihydro-2H-[1,2]thiazine 1-oxide 
• 2288-18-8 2-phenyl-1,3-butadiene 
• 884866-01-7 1-(4-methylbenzensulfonyl)-4-phenyl-1H-1,2,3-triazole 
• 109-92-2 ethyl vinyl ether 
• 941-55-9 4-toluenesulfonyl azide 
• 536-74-3 phenylacetylene 
• 121564-33-8 N-tosylfurfurylamine 
• 13707-47-6 2-furaldehyde tosylimine 
• 70-55-3 toluene-4-sulfonamide 
• 1584705-54-3 2-ethoxy-4-phenyl-1-tosyl-2,3-dihydro-1H-pyrrole 
• 4104-47-6 N-sulfinyl-p-toluenesulfonamide 
• 50487-71-3 4-methyl-N-(2-propenyl)benzenesulfonamide 
• 591-50-4 iodobenzene 

Downstream Products

• 27649-43-0 3-phenyl-1H-pyrrole 

Relevant academic research and scientific papers

CuI-Catalyzed Decarboxylative Thiolation of Propargylic Cyclic Carbonates/Carbamates to Access Allenyl Thioethers

The first CuI-catalyzed decarboxylative thiolation of terminal alkyne-substituted cyclic carbonates/carbamates to access allenes has been developed. A wide range of hydroxymethyl-and aminomethyl-containing allenyl thioethers were smoothly obtained in good to excellent yields under mild conditions. The copper-allenylidene intermediate among the process is crucial to the decarboxylative thiolation reaction. This method opens up a new channel to access allenyl thioether compounds.

A ring closing metathesis-manganese dioxide oxidation sequence for the synthesis of substituted pyrroles

The combination of ring closing, or enyne metathesis with oxidation in order to prepare N-sulfonyl pyrroles is described. Reasonable to good yields were obtained for a variety of substituents and the procedure may also be conducted in one-pot. 2-Bromo N-sulfonyl adducts prepared in this manner were subjected to an intramolecular Heck-type cyclisation, forming cyclic sulfonamides.

A gold-catalyzed 1,2-acyloxy migration/intramolecular cyclopropanation/ring enlargement cascade: Syntheses of medium-sized heterocycles

The synthesis of medium-sized heterocycles possessing a trans double bond is still a challenge. Herein, gold(I)-catalyzed 1,2-acyloxy migration/intramolecular cyclopropanation/ring enlargement cascade reaction of furans has been developed, providing highly efficient access to ten- and eleven-membered heterocycles with a broad substrate scope under mild reaction conditions. The reaction outcome features high chemoselectivity at the C5-position of furan. Moreover, a trans-double bond was embodied in the medium ring system.

Synthesis of pyrroles from terminal alkynes, N-sulfonyl azides, and alkenyl alkyl ethers through 1-sulfonyl-1,2,3-triazoles

A method for synthesis of substituted pyrroles has been developed. 1-Sulfonyl-1,2,3-triazoles generated from terminal alkynes gave α-imino rhodium carbene complexes, which when reacted with alkenyl alkyl ethers afforded substituted pyrroles. The method can be efficiently applied to a one-pot sequential reaction starting from terminal alkynes.

Rhodium-catalyzed transannulation of 1,2,3-triazoles to polysubstituted pyrroles

Rhodium-catalyzed transannulation of N-sulfonyl-1,2,3-triazoles with vinyl ether has been accomplished for the synthesis of various polysubstituted pyrroles. The present method allows the synthesis of mono-, di-, and trisubstituted pyrroles with appropriate substitutions. Furthermore, the developed methodology was applied in the formal synthesis of neolamellarin A, an antitumor agent.

Facile synthesis of pyrroles via Rh(II)-catalyzed transannulation of 1-tosyl-1,2,3-triazoles with silyl or alkyl enol ethers

A novel Rh(II)-catalyzed transannulation of 1-tosyl-1,2,3-triazoles with silyl or alkyl enol ethers has been developed, which enables the facile synthesis of substituted pyrroles in a regiocontrollable manner. Moreover, the methodology could be extended to access 3-pyrrolin-2-one derivatives with silyl ketene acetals used as the reaction partner.

A metathesis approach to aromatic heterocycles

The ring closing metathesis (RCM) reaction can be used to prepare substituted furans and pyrroles. By utilising a Pd-catalysed coupling reaction with methoxyallene, allylic alcohols and sulfonamides can be converted into substrates that are ideal precursors to ring closing metathesis. After the RCM reaction is complete, the addition of acid promotes an elimination of methanol to form the fully aromatised system. A range of different substitution patterns and functional groups are compatible with this sequence. Double allene coupling, RCM and elimination reactions are also possible and allow the formation of biaryl systems. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.

N-p-Toluenesulfonylpyrroles from 1,3-dienes

1,3-Dienes can be converted to N-p-toluenesulfonylpyrroles in two steps: 1) [4+2]-cycloaddition with N-sulfinyl-p-toluenesulfonamide and 2) conversion of the 3,6-dihydro-1,2-thiazine oxide adduct to a pyrrole using triethylamine-trimethylphosphite.