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Usage

InChI:InChI=1/C12H11NO3S/c1-10(14)12-8-5-9-13(12)17(15,16)11-6-3-2-4-7-11/h2-9H,1H3

Upstream product

• 16851-82-4 N-phenylsulfonylpyrrole 
• 98-09-9 benzenesulfonyl chloride 
• 64-19-7 acetic acid 
• 108-24-7 acetic anhydride 

Downstream Products

• 1072-83-9 2-Acetylpyrrole 
• 97188-25-5 1-Benzenesulfonyl-2-ethyl-1H-pyrrole 
• 103085-22-9 2-ethyl-1-(phenylsulfonyl)pyrrolidine 
• 131543-97-0 2-ethyl-1-(phenylsulfonyl)-3-pyrroline 
• 741288-81-3 1-(6-methoxy-pyridin-3-yl)-5-[1-(phenylsulfonyl)pyrrol-2-yl] pyrazole-3-carboxylic acid ethyl ester 
• 875553-34-7 4-[1-(phenylsulfonyl)-1H-pyrrol-2-yl]-2, 4-dioxobutanoic acid methyl ester 
• 1404195-34-1 7-chloro-4-methyl-3-(phenylsulfonyl)-3H-pyrrolo[2,3-c]quinoline 
• 1404195-30-7 C₁₈H₁₄ClIN₂O₂S 
• 1404195-24-9 4-methyl-3-(phenylsulfonyl)-3H-pyrrolo[2,3-c]quinoline 
• 1404195-27-2 3-((3-(phenylsulfonyl)-3H-pyrrolo[2,3-c]quinolin-4-yl)methyl)quinazolin-4(3H)-one 
• 1404195-26-1 4-((6-chloro-9H-purin-9-yl)methyl)-3-(phenylsulfonyl)-3H-pyrrolo[2,3-c]quinoline 
• 1404195-25-0 4-(bromomethyl)-3-(phenylsulfonyl)-3H-pyrrolo[2,3-c]quinoline 
• 1404195-23-8 2-iodo-N-(1-(1-(phenylsulfonyl)-1H-pyrrol-2-yl)ethylidene)aniline 
• 130896-50-3 1-Benzenesulfonyl-2-(1-trimethylsilanyloxy-vinyl)-1H-pyrrole 

Relevant academic research and scientific papers

Hydrogen bond donor solvents enabled metal and halogen-free Friedel–Crafts acylations with virtually no waste stream

We have developed a metal and halogen-free Friedel–Crafts acylation protocol with virtually no waste stream generation. We propose a hydrogen bonding donor solvent will form a hydrogen bonding network and may provide significant rate enhancement for Friedel–Crafts reactions. Trifluoroacetic acid is one of the strongest H-bond donor solvents, which is also volatile and can be easily recovered by distillation without need for reaction workup. Our protocol is a ‘green’ Friedel–Crafts acylation process: 1) the catalyst can be recovered and reused; 2) using halogen free starting material (carboxylic acids anhydride or carboxylic acids); 3) no need for aqueous reaction work-up; 4) minimum or no waste steam generation.

Lewis Acid Catalysis in Supercritical Carbon Dioxide. Use of Poly(ethylene glycol) Derivatives and Perfluoroalkylbenzenes As Surfactant Molecules Which Enable Efficient Catalysis in ScCO2

Lewis acid catalysis in supercritical carbon dioxide (CO2) was investigated. While solubility of most organic materials is low in scCO 2, poly(ethylene glycol) derivatives or perfluoroalkylbenzenes were found to work as surfactants to dissolve organic materials in scCO2. In the presence of these molecules, Lewis acid catalyzed organic reactions such as aldol-, Mannich-, and Friedel-Crafts-type reactions proceeded smoothly in scCO2. Formation of emulsions was observed in these reactions, and the systems were studied in detail.

Regioselective Synthesis of Acylpyrroles

The regioselective synthesis of several pyrrole derivatives is described.AlCl3-catalyzed acylation reactions of 1-(phenylsulfonyl)pyrrole (1) give 3-acyl derivatives, whereas the corresponding BF3*OEt2-catalyzed reactions give 2-acyl derivatives predominantly.Mild alkaline hydrolysis gives the corresponding acyl-1H-pyrroles in excellent yields.AlCl3-catalyzed reactions of 1 with 1,1-dichloromethyl methyl ether and oxalyl chloride give 1-(phenylsulfonyl)-2-formylpyrrole (6) and 1-(phenylsulfonyl)-2-(chlorocarbonyl)pyrrole (7), respectively. 3-Pyrrolylacetic acid (10) was prepared by thallium(III) nitrate promoted rearrangement of 1-(phenylsulfonyl)-3-acetylpyrrole (2a).Trifluoroacetic anhydride catalyzed cyclization of 4-butyric acid (14) gives 1-(phenylsulfonyl)-7-oxo-4,5,6,7-tetrahydroindole (17).Attempts to cyclize 14 at the 4-position have been unsuccessful.

PYRROLE CHEMISTRY XXV: A SIMPLIFIED SYNTHESIS OF SOME 3-SUBSTITUTED PYRROLES

A new synthesis is reported which allows the rapid preparation in good yield of 3-aroyl-, 3-acetyl- and 3-nitro- pyrroles from pyrrole utilizing the 1-benzenesulfonyl group as a blocking group.