6533b82ffe1ef96bd1294f85

RESEARCH PRODUCT

ChemInform Abstract: Exploiting the CNC Side Chain in Heterocyclic Rearrangements: Synthesis of 4(5)-Acylamino-imidazoles.

Nicolò VivonaSilvestre BuscemiAndrea PaceAntonio Palumbo Piccionello

subject

chemistry.chemical_classificationchemistryStereochemistryTransaminationSide chainGeneral MedicineCatalysis

description

A new variation on the Boulton-Katritzky reaction is reported, namely, involving use of a CNC side chain. A novel Montmorillonite-K10 catalyzed nonreductive transamination of a 3-benzoyl-1,2,4-oxadiazole afforded a 3-(alpha-aminobenzyl)-1,2,4-oxadiazole, which was condensed with benzaldehydes to afford the corresponding imines. In the presence of strong base, these imines underwent Boulton-Katritzky-type rearrangement to afford novel 4(5)-acylaminoimidazoles.

https://doi.org/10.1002/chin.201050123