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Org Lett. 2010 Aug 6;12(15):3491-3. doi: 10.1021/ol1013087.

Exploiting the CNC side chain in heterocyclic rearrangements: synthesis of 4(5)-acylamino-imidazoles.

Author information

1
Dipartimento di Chimica Organica E. Paternò, Università degli Studi di Palermo, Viale delle Scienze-Parco d'Orleans II, I-90128 Palermo, Italy. apalumbo@unipa.it

Abstract

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.

PMID:
20614866
DOI:
10.1021/ol1013087

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