ZnO Nanoparticles as an Efficient, Heterogeneous, Reusable, and Ecofriendly Catalyst for One-Pot, Three-Component Synthesis of 3,4-Dihydropyrimidin-2(1 H)-(thio)one Derivatives in Water

Article abstract of DOI:10.1080/00397911.2014.987350

An extremely efficient heterogeneous protocol is reported for the one-pot, three-component synthesis of a series of dihydropyrimidinones (DHPMs) in the presence of ZnO nanoparticles in water as a green solvent. The ZnO nanoparticles exhibited excellent ca

Full text of DOI:10.1080/00397911.2014.987350

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ZnO Nanoparticles as an Efficient, Heterogeneous,
Reusable, and Eco-Friendly Catalyst for One-Pot Three-
Component Synthesis of 3,4-Dihydropyrimidin-2(1H)-
(thio)one Derivatives in Water
Akbar Hassanpoura, Rahim Hosseinzadeh Khanmirib & Jafar Abolhasanic
a Department of Chemistry, Marand branch, Islamic Azad university, Marand, Iran
b Department of Chemistry, Shahid Beheshti University, Tehran, Iran
c Department of Chemistry, Tabriz branch, Islamic Azad university, Tabriz, Iran
Accepted author version posted online: 02 Dec 2014.
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To cite this article: Akbar Hassanpour, Rahim Hosseinzadeh Khanmiri & Jafar Abolhasani (2014): ZnO Nanoparticles
as an Efficient, Heterogeneous, Reusable, and Eco-Friendly Catalyst for One-Pot Three-Component Synthesis of 3,4-
Dihydropyrimidin-2(1H)-(thio)one Derivatives in Water, Synthetic Communications: An International Journal for Rapid
Communication of Synthetic Organic Chemistry, DOI: 10.1080/00397911.2014.987350
To link to this article: http://dx.doi.org/10.1080/00397911.2014.987350
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ZnO Nanoparticles as an Efficient, Heterogeneous, Reusable, and Eco-friendly
Catalyst for One-Pot three-Component Synthesis of 3,4-dihydropyrimidin-2(1H)-
(thio)one Derivatives in Water
Akbar Hassanpour1, Rahim Hosseinzadeh Khanmiri2, Jafar Abolhasani3
1Department of Chemistry, Marand branch, Islamic Azad university, Marand, Iran,
2Department of Chemistry, Shahid Beheshti University, Tehran, Iran, 3Department of
Chemistry, Tabriz branch, Islamic Azad university, Tabriz, Iran
Corresponding Author, Akbar Hassanpour, E-mail: hassanpour@marandiau.ac.ir
Abstract
An extremely efficient heterogeneous protocol is reported for the one-pot three-
component synthesis of a series of dihydropyrimidinones (DHPMs) in the presence of
ZnO nanoparticles in water as a green solvent. The ZnO nanoparticles exhibited excellent
catalytic activity and the proposed methodology is capable to providing the desired
products in high yield (65–94%) and short reaction time. After reaction course, ZnO
nanoparticles can be recycled and reused without any apparent loss of activity which
makes this ecofriendly process cost effective.
KEYWORDS: Biginelli reaction; Multicomponent reaction; ZnO nanoparticles; Green
chemistry; Dihydropyrimidinone
1. INTRODUCTION
During the past decade, multicomponent reactions (MCRs) gained significant interest
within the scientific community as an efficient, convenient, time-saving, and atom-
economical approach to a variety of drug-like heterocyclic molecules.[1] The acid-
catalyzed reaction of an aldehyde with enolizable ketones and urea to give a DHPM was
1

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first reported by Pietro Biginelli in 1893.[2] DHPMs compounds have a variety of
pharmaceutical properties including calcium channel modulation, mitotic kinesin Eg5
inhibition, antiviral and antibacterial properties.[2] Because of the above mentioned
properties of DHPMs, various synthetic methods with different catalysts have been
reported by different research groups. These catalysts are Brønsted acids,[3] Lewis
acids,[4] microwave variants,[5] Mn(OAc)2[3,6] LiBr,[7] ammonium salt,[8] solid support,[9]
CAN[10], NaCl,[11] and clay,[12] but some of the methods have their own limitations in
terms of yields, catalyst load, stability of promoters, etc.
NanoZnO is a very inexpensive and easily available Lewis acid and base catalyst
which has been widely used in organic reactions, especially as a catalyst in the Biginelli
reaction in water as solvent until now.[13] The surface of ZnO nanoparticles activate the
starting materials and coordination of accessible zinc cation to functional groups led to
their activation and enhancement of the reaction rates and yields.[14, 15, 16, 17] Due to the
importance of Biginelli products, the discovery and introduction of much mild, economic
and faster conditions with nano-catalysts are required. With the aim to develop an
operationally simple method for the synthesis of a large range of DHPMs, we report
herein a novel approach for synthesis of 3,4-dihydropyrimidin-2(1H)- (thio)ones (4) via
the one-pot reaction of ethyl acetoacetate (1), an aromatic or aliphatic aldehyde (2) and
urea or thiourea (3) using ZnO nanoparticles as a non-toxic nanocatalyst (Scheme 1).
2. RESULTS AND DISCUSSION
2