Journals / Turkish Journal of Chemistry / 2012 / Cilt: 36 - Sayı: 4

Three-component Passerini-Smiles coupling reaction of aldehydes and isocyanides with tropolone catalyzed by silica nanoparticles

Pages
537–544
DOI
—

Abstract

The use of Smiles rearrangement in Passerini-type couplings with tropolone allows very straightforward multicomponent formation of a-aryloxy amide derivatives. The 3-component addition of isocyanide to tropolone (2-hydroxy-2,4,6-cycloheptatrien-1-one) and aldehyde in the presence of silica nanoparticles (silica NP, ca. 70 nm) proceeds easily in methanol to form the title compounds in a new Passerini-Smiles-type reaction.

Özet

The use of Smiles rearrangement in Passerini-type couplings with tropolone allows very straightforward multicomponent formation of a-aryloxy amide derivatives. The 3-component addition of isocyanide to tropolone (2-hydroxy-2,4,6-cycloheptatrien-1-one) and aldehyde in the presence of silica nanoparticles (silica NP, ca. 70 nm) proceeds easily in methanol to form the title compounds in a new Passerini-Smiles-type reaction.

Keywords: Smiles rearrangement, Passerini-type coupling, tropolone, isocyanide, silica nanoparticles, Passerini-Smiles-type reaction