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

DOI

10.3906/kim-1202-8

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.

Keywords

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

First Page

779

Last Page

787

Recommended Citation

MASSOUDI, ABDOLHOSSAIN; AMINI, ISSA; RAMAZANI, ALI; and NASRABADI, FATEMEH ZEINALI (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: Vol. 36: No. 6, Article 1. https://doi.org/10.3906/kim-1202-8
Available at: https://journals.tubitak.gov.tr/chem/vol36/iss6/1