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A study of the friedel‐crafts acylation of 1‐benzenesulfonyl‐1 H ‐pyrrole in the preparation of 3‐aroylpyrroles
Author(s) -
Nicolaou Ioannis,
Demopoulos Vassilis J.
Publication year - 1998
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570350619
Subject(s) - chemistry , pyrrole , friedel–crafts reaction , acylation , chloride , hydrolysis , medicinal chemistry , organic chemistry , indole test , catalysis
In this work, we studied the aluminum chloride catalyzed reaction of 1‐benzenesulfonyl‐1 H ‐pyrrole with a series of eleven aroyl chlorides. The products formed were not isolated, but hydrolyzed to the target 3‐aroylpyrroles in overall yields, usually, higher than 50%. However, in the cases with the π electron rich 1‐phenyl‐1 H ‐pyrrole‐3‐carbonyl chloride and 1‐methyl‐1 H ‐indole‐3‐carbonyl chloride significant C‐2 substitution occured, resulting in the isolation of the corresponding 1‐benzenesulfonyl‐2‐aroylpyrroles as the predominant or the sole products. The desired C‐3 isomers were synthesized starting with 1‐triisopropylsilanyl‐1 H ‐pyrrole.