‐Pr‐AP: A new catalyst for the synthesis of
2‐amino‐4‐aryl thiazole derivatives
Ramin Ghorbani‐Vaghei | Sedigheh Alavinia | Zohreh Merati | Vida Izadkhah
Department of Organic Chemistry, Faculty
of Chemistry, Bu‐Ali Sina University,
Ramin Ghorbani‐Vaghei, Department of
Organic Chemistry, Faculty of Chemistry,
Bu‐Ali Sina University, 6517838683, Iran.
A simple and efficient synthesis of 2‐amino‐4‐aryl thiazole derivatives was
carried out through the reaction of substituted acetophenones and thiourea
using three different types of catalytic systems including N,N,N′,N′‐
tetrabromobenzene‐1,3‐disulfonamide [TBBDA], poly(N,N′‐dibromo‐N‐ethyl-
benzene‐1,3‐disulfonamide) [PBBS] and a combination of TBBDA and nano‐
magnetic catalyst supported with functionalized 4‐amino‐pyridine silica
‐Pr‐AP). The results showed that the use of TBBDA along with
‐Pr‐AP gains the highest yields of the products in the shortest
2‐Amino‐4‐aryl thiazole, magnetic nanoparticles, nano catalyst, solvent‐free, thiourea
1 | INTRODUCTION
The synthesis of organic compounds via green, mild, and
simple procedures is currently receiving considerable
attention of chemists. In recent years, the solvent‐free
organic reactions have captured great interests owing to
their many advantages including high efficiency and
selectivity, easy separation and purification, mild reaction
conditions, reduction in wastes, and benefits to the indus-
try and environment.
In recent decades, heterocyclic
compounds have attracted much attention because of
their abundance, and their increasing importance in the
field of pharmaceuticals
and chemical industries.
azole and its derivatives have been shown to possess a
broad range of biological activities. For example, thiamine
is known as vitamin B
, Ritonavir is an anti‐HIV agent,
and Nizatidine is an anti‐acid agent for the treatment of
gastroesophageal reflux disease (Figure 1).
Tchernic, Cook‐Heilborn, and Gabriel methods are some
common routes for the preparation of thiazoles.
now, these methods have been accomplished using differ-
ent catalysts such as Bismuth chloride,
Therefore, further development on the
environmental impact of the synthesis of thiazoles is of
interest and still in much demand.
Metal oxide nanostructures such as iron, have gained
significant importance as they have been demonstrated
to be applicable in catalytic technology which cannot be
usually achieved by their bulk counterparts.
uation of our research in the field of application of metal
nanoparticles as heterogeneous catalysts in organic
in this study, three convenient methods
for the one‐pot synthesis of 2‐amino‐4‐aryl thiazole
derivatives from substituted acetophenones and thiourea
are described in which TBBDA, PBBS, or a combination of
TBBDA and magnetic nanoparticles supported with
functionalized 4‐amino‐pyridine silica (MNPs@SiO
are investigated as catalytic systems.
2 | EXPERIMENTAL
2.1 | Materials and instrumentation
All commercially available chemicals were obtained
from Merck and Fluka companies and used without
further purification otherwise stated. Nuclear magnetic
resonance (NMR) spectra were recorded in DMSO‐d
Received: 11 July 2017 Revised: 3 September 2017 Accepted: 10 September 2017
Appl Organometal Chem. 2018;32:e4127.
Copyright © 2017 John Wiley & Sons, Ltd.wileyonlinelibrary.com/journal/aoc 1of10