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

Authors

ABDOLHOSSAIN MASSOUDI
ISSA AMINI
ALI RAMAZANI
FATEMEH ZEINALI NASRABADI

Abstract

The use of Smiles rearrangement in Passerini-type couplings with tropolone allows very straightforward multicomponent formation of \alpha-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.

DOI

10.3906/kim-1111-20

Keywords

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

First Page

537

Last Page

544

Recommended Citation

MASSOUDI, A, AMINI, I, RAMAZANI, A, & NASRABADI, F. Z (2012). Three-component Passerini-Smiles coupling reaction of aldehydes and isocyanides with tropolone catalyzed by silica nanoparticles. Turkish Journal of Chemistry 36 (4): 537-544. https://doi.org/10.3906/kim-1111-20