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Brønsted Acid‐Promoted Cascade Alkylation/Cyclization of Pyrroles with N , N ‐Dimethylaminomethyleneglutaconic Acid Dinitrile: A Concise Route to Cyclopenta[ b ]pyrroles
Author(s) -
Wu Kaikai,
Wu Ping,
Chen Jiping,
Sun Chenglin,
Yu Zhengkun
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500546
Subject(s) - chemistry , alkylation , pyrrole , brønsted–lowry acid–base theory , methyl iodide , medicinal chemistry , cascade , iodide , deamination , organic chemistry , stereochemistry , catalysis , chromatography , enzyme
A Brønsted acid ( p ‐TsOH⋅H 2 O) promoted alkylation/cyclization cascade reaction of pyrroles with N , N ‐dimethylaminomethyleneglutaconic acid dinitrile was efficiently realized to afford functionalized cyclopenta[ b ]pyrroles with excellent diastereoselectivity. Deamination of the corresponding ammonium salts of the cyclopenta[ b ]pyrroles with methyl iodide led to dihydrocyclopenta[ c ]pyrroles. The cascade reaction pathway was confirmed by isolation and transformation of the reaction intermediate, i.e., the 2‐alkylated pyrrole.