G Model
CCLET-2507; No. of Pages 4
Chinese Chemical Letters
Original article
Entirely green protocol for the synthesis of
saccharose as a homogenous catalyst
b-aminoketones using
*
Mir Rasul Mousavi, Nourallah Hazeri , Malek Taher Maghsoodlou, Sajjad Salahi,
Sayyed Mostafa Habibi-Khorassani
Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, P.O. Box 98135-674, Zahedan, Iran
A R T I C L E I N F O
A B S T R A C T
Article history:
Saccharose was applied as an efficient and homogenous catalyst for a one-pot, three-component
Received 11 January 2013
Received in revised form 27 February 2013
Accepted 5 March 2013
Available online xxx
Mannich reaction for the formation of
b-aminoketones from aromatic aldehydes, anilines, and
acetophenone at ambient temperature in excellent yields. This protocol has the following advantages:
mild conditions, high yields, clean reaction profiles, operational simplicity, and environmentally benign
and simple work-up procedures.
ß 2013 Nourallah Hazeri. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights
reserved.
Keywords:
Saccharose
b
-Amino carbonyl compounds
Mannich reaction
Three-component reaction
1. Introduction
Herein we present an eco-friendly, simple and efficient method for
the synthesis of b-amino carbonyl compounds via a one-pot three-
The Mannich reaction is a very useful tool for the development
and synthesis of several molecules [1]. Also this reaction is an
important carbon–carbon bond forming reaction in organic
synthesis for the preparation of various nitrogen-containing
natural products and the intermediates for significant pharma-
component reaction using aromatic aldehydes, anilines and
acetophenone in the presence of saccharose in water/ethanol at
room temperature (Scheme 1).
Recently, organic reactions in green solvents such as water,
ethanol and their mixtures devoid of harmful organic solvents in
the presence of green catalysts have attracted much attention,
because these solvents are cheap, safe, and environmentally
benign [28,29]. For this reason, we focused our investigation to
ceuticals [2–4].
nitrogen-containing compounds that can be assembled via
Mannich type reactions. -Amino carbonyl moieties are found
b-Amino carbonyl compounds are important
b
in a number of biologically active natural products [5]. Therefore,
much consideration has been drawn to the development of new
synthetic methods to prepare these compounds. The synthesis of
developing green new synthetic methods for the preparation of b-
aminoketones. This is a one-pot reaction in water/ethanol, which is
not only operationally simple, clean and efficient but also
consistently gives the corresponding products in good to excellent
yields.
various
b-amino carbonyl compounds has been reported using
three component reactions in the presence of Bro¨nsted acid, ionic
liquid, and CeCl3Á7H2O, etc. [6–27]. However, some of these
methods suffer from certain disadvantages and limitations such as
high cost, high catalyst loading, low yields, poor availability of the
catalysts, incompatibility with the environment and long reaction
2. Experimental
General procedure for the synthesis b-aminoketones 4: To mixture
time. Owing to the importance of
b-amino carbonyl compounds
of acetophenone 1 (1 mmol), aromatic aldehydes 2 (1 mmol) and
anilines 3 (1 mmol) in 5 mL water/ethanol was added saccharose
(15 mol%). The mixture was stirred at room temperature for an
appropriate amount of time. When the reaction completed as
indicated by TLC analysis, the reaction products were collected by
filtration. The products were washed with water/ethanol (50:50,
3 Â 2 mL) to give the corresponding pure compounds. The catalyst
remained in the water/ethanol filtrate.
from a pharmaceutical and biological point of view, there is still the
need to develop efficient, mild and environmentally benign
protocols for the synthesis of
b-amino carbonyl compounds.
* Corresponding author.
1001-8417/$ – see front matter ß 2013 Nourallah Hazeri. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
Please cite this article in press as: M.R. Mousavi, et al., Entirely green protocol for the synthesis of
b-aminoketones using saccharose as a