One-pot, three-component synthesis of 2,3-dihydro-4(1H)-quinazolinones by montmorillonite K-10 as an efficient and reusable catalyst

Article abstract of DOI:10.1080/00397910600639752

A wide range of mono- and disubstituted dihydroquinazolinones were synthesised via condensation of isatoic anhydride, primary amines, or ammonium salts with aromatic aldehydes in the presence of montmorillonite K-10. The catalyst is reusable and could be recycled for several runs without any decrease in its efficiency. Copyright Taylor & Francis Group, LLC.

Full text of DOI:10.1080/00397910600639752

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One‐Pot, Three‐Component Synthesis
of 2,3‐Dihydro‐4(1H)‐quinazolinones by
Montmorillonite K‐10 as an Efficient and
Reusable Catalyst
Peyman Salehi a , Minoo Dabiri b , Mostafa Baghbanzadeh b & Mahboobeh
Bahramnejad b
a Department of Phytochemistry, Medicinal Plants and Drugs Research
Institute, Shahid Beheshti University, Evin, Tehran, Iran
b Department of Chemistry, Faculty of Science, Shahid Beheshti University,
Evin, Tehran, Iran
Version of record first published: 22 Sep 2006.
To cite this article: Peyman Salehi , Minoo Dabiri , Mostafa Baghbanzadeh & Mahboobeh Bahramnejad
(2006): One‐Pot, Three‐Component Synthesis of 2,3‐Dihydro‐4(1H)‐quinazolinones by Montmorillonite
K‐10 as an Efficient and Reusable Catalyst, Synthetic Communications: An International Journal for Rapid
Communication of Synthetic Organic Chemistry, 36:16, 2287-2292
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Synthetic Communicationsw, 36: 2287–2292, 2006
Copyright # Taylor & Francis Group, LLC
ISSN 0039-7911 print/1532-2432 online
DOI: 10.1080/00397910600639752
One-Pot, Three-Component Synthesis
of 2,3-Dihydro-4(1H)-quinazolinones by
Montmorillonite K-10 as an Efficient
and Reusable Catalyst
Peyman Salehi
Department of Phytochemistry, Medicinal Plants and Drugs Research
Institute, Shahid Beheshti University, Evin, Tehran, Iran
Minoo Dabiri, Mostafa Baghbanzadeh, and Mahboobeh Bahramnejad
Department of Chemistry, Faculty of Science, Shahid Beheshti
University, Evin, Tehran, Iran
Abstract: A wide range of mono- and disubstituted dihydroquinazolinones were
synthesised via condensation of isatoic anhydride, primary amines, or ammonium
salts with aromatic aldehydes in the presence of montmorillonite K-10. The catalyst
is reusable and could be recycled for several runs without any decrease in its efficiency.
Keywords: 2,3-Dihydroquinazolin-4(1H)-ones, heterogeneous catalysis, montmoril-
lonite K-10
INTRODUCTION
Compounds with biological activity are often derived from heterocyclic struc-
tures. Indeed, one of the richest sources of diversity for medicinal chemists is
small heterocyclic rings, which, in addition to often exhibiting biological
activity, may serve as rigid scaffolds for further display of functionalities.
Received in the U.K. August 16, 2005
Address correspondence to Peyman Salehi, Department of Phytochemistry,
Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, Evin,
P.O. Box 19835-389, Tehran, Iran. E-mail: p-salehi@cc.sbu.ac.ir
2287

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2288
P. Salehi et al.
2,3-Dihydroquinazolinones are one such class of heterocycles that
attracted much attention because they have been reported to possess a wide
range of pharmaceutical activities including antifertility, antibacterial,
antitumor, antifungal, and mono amine oxidase inhibitory activity.[1–4]
There are several methods for the preparation of this class of compounds.
Among them, the most direct procedure includes condensation of aryl, alkyl,
and heteroaryl aldehydes with anthranilamide in the presence of p-toluene-
sulfonic acid as a catalyst.[5,6] Reductive cyclization of o-nitrobenzamide or
o-azidobenzamide with metallic samarium and catalytic amounts of iodine
was also used for the synthesis of 2,3-dihydroquinazolinones.[7] On the basis
of this procedure, Shi et al. has reported a new method for the synthesis of
these compounds.[8]
The use of heterogeneous and reusable catalysts represents one of the
most powerful and green procedures in chemical technology. Environmentally
benign solid catalysts such as clays and zeolites instead of mineral acids are
employed for acid-catalyzed organic reactions.[9]
Montmorillonite K-10 is the most important smectite used in catalytic
reactions. High cation-exchange capacity (CEC) and good swelling properties
allow the existence of a wide variety of catalytically active forms of montmor-
illonite (containing acidic cations, metal complexes, photocatalysts, active
cations, etc.).[10]
RESULTS AND DISCUSSION
In continuation of our investigations on the use of heterogeneous catalysts for
the fine chemical preparation,[11–15] here one-pot condensation of primary
amines or ammonium salts and aromatic aldehydes with isatoic anhydride
in the presence of montmorillonite K-10 is reported. The reactions were
carried out in refluxing ethanol, and the corresponding mono- and disubsti-
tuted derivatives of 2,3-dihydro-4(1H)-quinazolinone were obtained in high
yields.
The use of ammonium salts as a productive source of ammonia in
synthetic reactions has been well known for a long time.[16–19] Similarly,
monosubstituted 2,3-dihydro-4(1H)-quinazolinones were synthesized effi-
ciently by the condensation of isatoic anhydride and aromatic aldehydes in
the presence of ammonium salts and montmorillonite K-10 under hetero-
geneous conditions (Scheme 1). The results are summarized in Table 1.
To compare the efficiency of ammonium salts, the reactions were carried
out with different counter ions such as carbonate, acetate, and chloride
under the same conditions. In all cases, monosubstituted 2,3-dihydro-4(1H)-
quinazolinones were produced in good yields; however, the best yields were
obtained with ammonium carbonate (Table 1).
Moreover, treatment of isatoic anhydride and aryl aldehydes with primary
aliphatic and aromatic amines in the presence of montmorillonite K-10 in

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2,3-Dihydro-4(1H)-quinazolinones
2289
Scheme 1.
refluxing ethanol afforded disubstituted derivatives of 2,3-dihydro-4(1H)-qui-
nazolinone in good yields (Scheme 2). The results are represented in Table 2.
Aliphatic and aromatic amines afforded the products in good yields.
However, aliphatic amines gave the products in shorter periods in comparison
with aromatic amines, probably because of their higher nucleophilicity.
To investigate the possibility of recycling the catalyst, an investigation
was made on the reaction of isatoic anhydride, ethylamine, and
Table 1. Synthesis of monosubstituted 2,3-dihydroquinazolin-4(1H)-ones with
different ammonium salts in the presence of montmorillonite K-10 in ethanol
Time
(h)
Yielda
(%)
Entry
R1
X
Mp (8C)
1
2
Ph
4-ClC6H4
CO232
4
5
7
4
5
5
4
4
5
7
4
5
5
4
4
5
7
4
5
5
4
85
95
85
77
75
80
80
72
80
73
72
73
75
77
70
77
73
70
70
73
75
218–220[9]
198–200[9]
178–180[9]
165–167[3]
233–234[19]
210–213[3]
165–167[19]
218–220[9]
198–200[9]
178–180[9]
165–167[3]
233–234[19]
210–213[3]
165–167[19]
218–220[9]
198–200[9]
178–180[9]
165–167[3]
233–234[19]
210–213[3]
165–167[19]
CO232
3
4-CH3OC6H4
2-CH3OC6H4
4-CH3C6H4
3,4-(CH3O)2C6H3
2-Furyl
CO232
4
CO232
5
CO232
6
CO232
7
CO232
8
Ph
4-ClC6H4
CH3COO2
CH3COO2
CH3COO2
CH3COO2
CH3COO2
CH3COO2
CH3COO2
Cl2
9
10
11
12
13
14
15
16
17
18
19
20
21
4-CH3OC6H4
2-CH3OC6H4
4-CH3C6H4
3,4-(CH3O)2C6H3
2-Furyl
Ph
4-ClC6H4
Cl2
4-CH3OC6H4
2-CH3OC6H4
4-CH3C6H4
3,4-(CH3O)2C6H3
2-Furyl
Cl2
Cl2
Cl2
Cl2
Cl2
aIsolated yield.