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Synthesis of Furans and Pyrroles from 2‐Alkoxy‐2,3‐dihydrofurans Through a Nucleophilic Substitution‐Triggered Heteroaromatization
Author(s) -
Liu Changhui,
Zhou Li,
Huang Wenbo,
Wang Man,
Gu Yanlong
Publication year - 2016
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.201500993
Subject(s) - chemistry , nucleophilic substitution , nucleophile , alkoxy group , nucleophilic aromatic substitution , substitution reaction , pyrrole , furan , combinatorial chemistry , bromide , medicinal chemistry , ring (chemistry) , organic chemistry , catalysis , alkyl
An effective method to synthesize α‐functionalized furan and pyrrole derivatives was developed using 2‐alkoxy‐2,3‐dihydrofurans as modular precursors. This protocol featured a previously unreported tandem nucleophilic substitution/heteroaromatization reaction. Nucleophiles such as indole, α‐oxoketene dithioacetal, trimethoxybenzene, and dimethoxynaphthalene can react readily with 2‐alkoxy‐2,3‐dihydrofurans to afford α‐functionalized five‐membered ring heterocycles in the presence of acid catalysts, such as copper bromide and iron chloride. The mechanism of the reaction was also discussed, in which the first step, nucleophilic substitution, is the key in triggering the succeeding heteroaromatization. This method can also be extended to the synthesis of dihydrothiophenes.