Preparation of 2-(N,N-dialkylamino)-2,4,6- cycloheptatrien-1-one derivatives from an isocyanide, a primary amine, propionaldehyde, and tropolone via Ugi-Smiles coupling reaction in the presence of silica nanoparticles

Authors

ABDOLHOSSAIN MASSOUDI
ISSA AMINI
ALI RAMAZANI
FATEMEH ZEINALI NASRABADI

Abstract

The use of Smiles rearrangement in Ugi-type couplings with tropolone allows very straightforward multicomponent formation of 2-(N,N-dialkylamino)-2,4,6-cycloheptatrien-1-one derivatives. The 4-component reaction of isocyanides, tropolone (2-hydroxy-2,4,6- cycloheptatrien-1-one), primary amines, and propionaldehyde in the presence of silica nanoparticles (silica NPs, ca. 42 nm) proceeds easily in methanol to form the title compounds in a new Ugi--Smiles-type reaction.

DOI

10.3906/kim-1202-8

Keywords

Ugi-type coupling, tropolone, isocyanides, primary amines, silica (NP), Ugi--Smiles-type reaction

First Page

779

Last Page

787

Recommended Citation

MASSOUDI, A, AMINI, I, RAMAZANI, A, & NASRABADI, F. Z (2012). Preparation of 2-(N,N-dialkylamino)-2,4,6- cycloheptatrien-1-one derivatives from an isocyanide, a primary amine, propionaldehyde, and tropolone via Ugi-Smiles coupling reaction in the presence of silica nanoparticles. Turkish Journal of Chemistry 36 (6): 779-787. https://doi.org/10.3906/kim-1202-8