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

6533b874fe1ef96bd12d63ae

RESEARCH PRODUCT

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

Silvestre Buscemi Antonio Palumbo Piccionello Nicolò Vivona Andrea Pace

subject

chemistry.chemical_classification chemistry Transamination Stereochemistry Organic Chemistry Side chain Settore CHIM/06 - Chimica Organica Physical and Theoretical Chemistry oxadiazole imidazole heterocyclic rearrangement transamination heterogeneous catalysis Biochemistry Catalysis

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.

year	journal	country	edition	language
2010-07-08	Organic Letters

https://doi.org/10.1021/ol1013087

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