86695-72-9

Upstream product

• 16851-82-4 N-phenylsulfonylpyrrole 
• 1490-25-1 succinic acid monomethylester chloride 
• 30000-64-7 methyl 4-oxo-4-(1H-pyrrol-2-yl)butanoate 
• 98-09-9 benzenesulfonyl chloride 

Downstream Products

• 71739-65-6 4-oxo-4-(1H-pyrrol-2-yl)butanoic acid 
• 86688-92-8 4-<1-(Phenylsulfonyl)-2-pyrrolyl>-4-oxobutyric acid 
• 86688-87-1 Methyl 4-<1-(Phenylsulfonyl)-3-pyrrolyl>-4-oxobutyrate 

Relevant academic research and scientific papers

Bu3SnH-mediated radical cyclisation onto azoles

Alkyl radicals have been cyclised onto pyrroles, imidazoles and pyrazoles, and acyl radicals cyclised onto pyrroles, using Bu3SnH-, (TMS)3SiH- and Bu3GeH-mediated aromatic homolytic substitution for the synthesis of bicyclic N-heterocycles. The reactions yield intermediate π-radicals that lose hydrogen in the?rearomatisation step of the aromatic homolytic substitution. Mechanistic studies of these rearomatisation steps indicate aromatic homolytic substitution in which the initiator or breakdown products from the inhibitor are responsible for the H-abstraction step.

Ring-deactivated hydroxymethylpyrroles as inhibitors of α-chymotrypsin

N-Acyl and N-sulfonylhydroxymetyhylpyrroles have been synthesised and shown to inhibit α-chymotrypsin. A hydrophobic group in the N-substituent has been shown to be required for activity. Copyright

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.