An efficient an one-pot method for synthesis of 2-Aryl-(3H)-4-quinazolinones derivatives catalyzed by SSA

Article abstract of DOI:10.13005/ojc/300259

A mixture of 2-amino benzamide with aromatic aldehyds in the presence of SSA under solvent-free condition were converted to quinazolinones with good yields.

Full text of DOI:10.13005/ojc/300259

ISSN: 0970-020 X
CODEN: OJCHEG
2014, Vol. 30, No. (2):
Pg. 833-835
ORIENTAL JOURNAL OF CHEMISTRY
An International Open Free Access, Peer Reviewed Research Journal
www.orientjchem.org
An Efficient an One-Pot Method for Synthesis of
2-Aryl-(3H)-4-Quinazolinones Derivatives Catalyzed by SSA
FARHAD HATAMJAFARI* and SIMA ESLAMI
Department of Chemistry, Faculty of Science,
Islamic Azad University-Tonekabon Branch, Tonekabon, Iran.
*Corresponding author E-mail: hatamjafari@yahoo.com
http://dx.doi.org/10.13005/ojc/300259
(Received: February 02, 2014; Accepted: March 04, 2014)
ABSTRACT
A mixture of 2-amino benzamide with aromatic aldehyds in the presence of SSA under
solvent-free condition were converted to quinazolinones with good yields.
Key words: Starch SulphuricAcid (SSA), (3H)-4-Quinazolinones, One-pot, Solvent-Free .
INTRODUCTION
used in the synthesis of quinazolinone derivatives6-
.
14
Natural compounds with quinazoline
structural motif have been identified to display a
wide range of biological activities. The prominent
potencies associated with quinazoline containing
compounds are their anticancer,anti-inflammatory,
anthelmintic, analgesic, and anticonvulsive
The early method, based on the reaction
of 2-aminobenzamide with aldehyds, was
performed in the presence of H2SO4 and as a
requirement of its refluxing condition much excess
of aldehyds was used15.Though an excess of
aldehyds is necessary to diminish the intermolecular
side-reactions, the conventional beating method
ever needs additional aldehyds both to improve
the yield. In contrast to the Liquid H2SO4, which is
difficult to recovery and takes some effort in work-
up, the silica-supported H2SO4, can be easily
separated and recycled without the loss of activity
for several times. Thus, 2-aminobenzamides (1)
reacted with nearly 2 equivalents of aromatic
aldehyds(2) with the aide of SiO2/H2SO4 and
activities1-5
.
We now report that cyclocondensation of
2-aminobenzamides (1) with aromatic aldehyds(2)
on silica-supported sulfuric acid quickly provides
the substituted quinazolin-4(3H)-ones (3) in fairly
high yields. To our knowledge there has been
reported on the use of sulfuric acid adsorbed on
silica gel (SiO2/H2SO4)as a solid catalyst in the
synthesis of quinazolines. Various catalysts were

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HATAMJAFARI & ESLAMI , Orient. J. Chem., Vol. 30(2), 833-835 (2014)
submission to microwave irradiation to provide fairly used to replace for synthesis quinazolinones.
high yields of substituted quinazolin-4(3H)-ones Previously, we have synthesized a number of
(2a-d) in 25 minutes.
heterocyclic compounds16-28. Herein we report some
of quinazolinones at one pot reaction,
However, these reactions often require environmentally friendly with high yields and easy
harsh conditions and long reaction time and low separation (Scheme 1).
efficiency can. Aromatic aldehydes, especially when
Scheme 1:
General Procedure for the Preparation of (3H)-4- °C, FT-IR (Vmax/cm-1) (KBr disc):3410 (amid .NH str.);
Quinazolinone Derivatives
3078 (arom. CH str.); 1670(amid. C=O Str.);
A mixture of aldehyde (1 mmol) and2- 1648(C=N Str.).1H NMR ( 400.13 MHz, DMSO):
amino benzamide (1 mmol), and starch sulphuric =7.53(1H, t, 3J =7.8, 1CH); 7.63(2H, d, 3J =7.8, 2CH);
acid (20 W%) as a catalyst was stirred at 80 oC for 7.75(1H, d,3J=7.8 1CH); 7.84(1H, t, J =7.8, 1CH);
3
25 min. The progress of reaction was monitored by 8.16(1H, d, 3J =7.8, 1CH); 8.21(2H, d, 3J =7.8, 2CH);
TLC. After finishing, recrystallized from ethanol 95% 11.54(1H, s, NH).
to give pure products (2a-d)
2-(4-nitrophenyl)-(3H)-4-Quinazolinone (2d)
2-(3-nitrophenyl)-(3H)-4-Quinazolinone (2a)
Pale yellow crystals, Yield: 69%, m.p=361-
Pale Blue crystals, Yield: 87%, m.p> 300 363°C,FT-IR (Vmax/cm-1) (KBr disc): 3380(amid. NH
°C, FT-IR (Vmax/cm-1) (KBr disc): 3440(amid NH Str.); Str.); 3050(arom. CH Str); 1678(amid. C=O Str.);
3092(arom CH Str.); 1682(amid C=O Str.); 1635(C=N Str.); 1530, 1355(N-O Str.).H NMR (
1640(C=N Str.); 1520, 1360(N-O Str.).1H 400.13 MHz, DMSO):  =7.56(1H, t, 3J= 7.2, 1CH);
NMR(400.13MHz, DMSO): = 7.56 (1H, t, 3J= 8Hz, 7.78(1H, d, 3J = 7.2, 1CH); 7.86(1H, t, 3J = 7.2, 1CH);
1CH); 7.79-7.88 (3H, m, 3CH); 8.17(1H, d, 3J = 8Hz, 8.17(1H, d,3J = 7.2, CH); 8.37-8.42(4H, dd,3J = 8.8,
1CH); 8.42(1H, d, 3J = 8Hz, 1CH); 8.61(1H, d, 3J = CH); 11.41(1H, s, NH).
8Hz, 1CH); 9.02(1H, s, 1CH); 11.82 (1H, s, NH).
In conclusion, in comparison with the
2-(4-methoxyphenyl)-(3H)-4-Quinazolinone (2b)
precedent related methods which show drawbacks
Yellow crystals, Yield: %72, m.p= 245-248 from the standpoints of, prolong refluxing in solvent,
°C, FT-IR (Vmax/cm-1) (KBr disc):3410 (amid NH Str.); need to inert gas, and consuming more aldehyds,
3131(arom.CH Str.);2990(aliph.CH Str.);1675(amid the notable advantages of this methodology are:
C=O Str.);1643(C=N Str.).
mild conditions in a solvent-free system, fairly high
yields, fast reaction, no aqueous work-up and safe
and environmental friendly conditions.
2-(4-chlorophenyl)-(3H)-4-Quinazolinone (2c)
White crystals, Yield: 89%, m.p = 302-304
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