New and efficient palladium(0)-mediated microwave-assisted direct C3 alkenylation of imidazo[1,2-a]pyridines

In this paper, we present the synthesis of 3-alkenylimidazo[1,2-a]pyridines in high to moderate yields by microwave direct palladium-catalyzed C-H alkenylation between bromoalkenes and imidazo[1,2-a]pyridines. The scope and limitation of the palladium(0)-catalyzed alkenylation method were investigat...

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 16; pp. 2537 - 2542
Main Authors Koubachi, Jamal, El Kazzouli, Said, Berteina-Raboin, Sabine, Mouaddib, Abderrahim, Guillaumet, Gerald
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 18.08.2008
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
palladium-catalyzed coupling
SERIES
NUCLEOSIDES
alkenylation
SELECTIVE LIGANDS
POTENT
BINDING-AFFINITY
PALLADIUM-CATALYZED ARYLATION
microwave irradiation
ANTIVIRAL ACTIVITY
ANTIULCER AGENTS
INHIBITORS
imidazo[1,2-a]pyridines
DERIVATIVES
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Summary:In this paper, we present the synthesis of 3-alkenylimidazo[1,2-a]pyridines in high to moderate yields by microwave direct palladium-catalyzed C-H alkenylation between bromoalkenes and imidazo[1,2-a]pyridines. The scope and limitation of the palladium(0)-catalyzed alkenylation method were investigated. Optimized conditions were successfully applied to a wide variety of imidazo[1,2-a]pyridine derivatives and bromoalkenes. The compatibility of the synthesis with the presence of a chloro substituent in the 6-position was investigated. The 6-chloroimidazo[1,2-a]pyridines were functionalized using Suzuki cross-coupling conditions to give polyfunctional compounds.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-2008-1067181