Synthesis and Chemistry of 4,5-Dimagnesioimidazole Dianions

Synthesis and Chemistry of 4,5-Dimagnesioimidazole Dianions

An experimentally convenient procedure for the generation of 4,5-dimagnesioimidazoles is described. N-Protected 2-substituted 4,5-diiodoimidazoles were treated with i-PrMgCl (2.4 equiv) in THF at 0−5 °C. The resulting vicinal dianions reacted with electrophiles to give 4,5-disubstituted imidazoles i...

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Veröffentlicht in:Journal of organic chemistry 2002-04, Vol.67 (8), p.2699-2701
Hauptverfasser: Butz, Ralf H.-J, Lindell, Stephen D
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Organic chemistry
Preparations and properties
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Zusammenfassung:An experimentally convenient procedure for the generation of 4,5-dimagnesioimidazoles is described. N-Protected 2-substituted 4,5-diiodoimidazoles were treated with i-PrMgCl (2.4 equiv) in THF at 0−5 °C. The resulting vicinal dianions reacted with electrophiles to give 4,5-disubstituted imidazoles in 27−71% yields.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0161680