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Microwave‐Assisted Solid‐Phase Synthesis of a 1,2‐Disubstituted Benzimidazole Library by Using a Phosphonium Linker
Author(s) -
Ríos Natalia,
Chavarría Cecilia,
Gil Carmen,
Porcal Williams
Publication year - 2013
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.1619
Subject(s) - chemistry , benzimidazole , phosphonium , triphenylphosphine , linker , solid phase synthesis , iodide , yield (engineering) , microwave irradiation , methyl iodide , combinatorial chemistry , microwave , phase (matter) , polymer chemistry , organic chemistry , nuclear chemistry , catalysis , peptide , biochemistry , materials science , physics , quantum mechanics , computer science , metallurgy , operating system
An efficient and rapid microwave-assisted solid-phase method for the synthesis of 5-methyl-1,2-disubstituted benzimidazoles derivatives has been developed. The phosphonium linker, obtained by reaction between polymer-supported triphenylphosphine and 4-fluoro-3-nitrobenzyl iodide, underwent aromatic substitution with primary amines, followed by one-pot reaction with aldehydes in the presence of SnCl2·2H 2O, yielded the benzimidazole system under microwave irradiation. The final products were released from the resin with NaOH under microwave irradiation and were obtained in high purity and good overall yield. © 2013 HeteroCorporation.Peer Reviewe