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

DOI

10.3906/kim-1111-20

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.

Keywords

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

First Page

537

Last Page

544

Recommended Citation

MASSOUDI, ABDOLHOSSAIN; AMINI, ISSA; RAMAZANI, ALI; and NASRABADI, FATEMEH ZEINALI (2012) "Three-component Passerini-Smiles coupling reaction of aldehydes and isocyanides with tropolone catalyzed by silica nanoparticles," Turkish Journal of Chemistry: Vol. 36: No. 4, Article 5. https://doi.org/10.3906/kim-1111-20
Available at: https://journals.tubitak.gov.tr/chem/vol36/iss4/5