: A recyclable magnetic heterogeneous
nanocatalyst for synthesis of β‐amino carbonyl derivatives
and synthesis of benzylamino coumarin derivatives through
Hossein Ghafuri | Behnaz Ghorbani | Afsaneh Rashidizadeh | Majid Talebi | Mahdi Roshani
Catalysts and Organic Synthesis Research
Laboratory, Department of Chemistry,
Iran University of Science and
Technology, P.O. Box 16846‐13114,
Tehran, I. R., Iran
Hossein Ghafuri, Catalysts and Organic
Synthesis Research Laboratory,
Department of Chemistry, Iran University
of Science and Technology, P.O. Box
16846‐13114 Tehran, I. R. Iran.
Research Council of the Iran University of
Science and Technology
In the present work, we developed an effective protocol for the synthesis of β‐
amino carbonyl compounds and synthesis of benzylamino coumarin deriva-
tives through Mannich type reaction in high yields. Fe
employed as an effective heterogeneous nanocatalyst for the Mannich reaction.
This research consists of two sections. In first section, β‐amino carbonyl deriv-
atives were synthesized under solvent‐free condition. In the other section,
benzylamino coumarin compounds were synthesized at room temperature.
The present approach offers several advantages such as short reaction times,
low cost, easy work‐up, mild reaction conditions, high yields and ease of recov-
ery and reusability of the catalyst without significant loss of activity.
Mannich reaction, Fe
, heterogeneous nanocatalyst, recyclable catalyst, β‐amino
1 | INTRODUCTION
The synthesis of pharmaceuticals, natural molecules and
other nitrogenous biologically active compounds is an
important field in organic synthesis. The Mannich reac-
tion provides significant protocols for the synthesis of
Usually in this reaction, an amine,
two carbonyl compounds and acid (or base) catalysts are
used to afford various β‐amino carbonyl compounds.
β‐amino carbonyl compounds forming from Mannich
reaction are significant synthetic intermediates for
various pharmaceuticals and natural products.
Benzylamino coumarin and its derivatives are formed
through Mannich type reactions. They are important
members of heterocyclic compounds family. These com-
pounds are biologically active and have many properties
such as: anti‐HIV,
Hence, the devolvement of novel synthetic methods
leading to β‐amino carbonyl compounds and their deriva-
tives including benzylamino coumarin have become cen-
ter of attentions. From these methods, one‐pot three‐
component reaction strategy is reliable and promising
which allows for a wide range of structural variations.
Various catalyst systems were examined for the catalytic
three‐component Mannich reaction including NbCl
silica sulfuric acid,
To the best of our knowledge only
a few remarkable researches on synthesis of benzylamino
coumarin derivatives have been reported.
It is note-
worthy that the most of reported methods for the synthe-
sis of β‐amino carbonyl compounds and benzylamino
coumarin derivatives have some drawbacks such as: lon-
ger reaction time, inadequate yields, use of expensive cat-
alyst and limited success in term of stereoselectivity.
Therefore, development of an effective and affordable
Received: 19 July 2017 Revised: 18 September 2017 Accepted: 23 September 2017
Appl Organometal Chem. 2018;32:e4147.
Copyright © 2017 John Wiley & Sons, Ltd.wileyonlinelibrary.com/journal/aoc 1of14