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European	Journal	of	Chemistry	4	(4)	(2013)	462‐466	

European	Journal	of	Chemistry	
ISSN	2153‐2249	(Print)	/	ISSN	2153‐2257	(Online)		2013	EURJCHEM	

DOI:10.5155/eurjchem.4.4.462‐466.847	

	
	

	

	

European	Journal	of	Chemistry	
Journal	homepage:	www.eurjchem.com	

	 	 	

Polyethylene	glycol	(PEG‐400)	as	a	medium	for	novel	and	efficient	synthesis	of	
2‐phenyl‐2,3‐dihydroquinazolin‐4(1H)‐one	derivatives	

Parthasaradhi	Yerram,	Rakhi	Chowrasia,	Suresh	Seeka	and	Savitha	Jyostna	Tangenda	*	

Department	of	Chemistry,	Kakatiya	University,	Warangal,	Pin,	506009,	India	

*	Corresponding	author	at:	Department	of	Chemistry,	Kakatiya	University,	Warangal,	Pin,	506009,	India.		
Tel.:	+91.0870.2461419;	fax:	+91.0870.2461419.	E‐mail	address:	savithajyostna@gmail.com	(S.J.	Tangenda).	

	
	

	 	

	 	 	
COMMUNICATION	INFORMATION	 	 ABSTRACT
Received:	06	June	2013	
Received	in	revised	form:	24	July	2013	
Accepted:	26	July	2013	
Online:	31	December	2013	

KEYWORDS	

	 A	 novel,	 efficient	 synthesis	 of	 2‐phenyl‐2,	 3‐dihydroquinazolin‐4(1H)‐one	 derivatives	 is
reported	 for	 the	first	 time	 in	PEG‐400	by	 the	 reaction	of	various	aldehydes,	 anthranilamide
under	catalyst‐free	conditions	and	the	formation	of	product	good	to	excellent	yields.	PEG‐400
can	be	recovered	and	reused	without	any	significant	loss	of	activity.	

PEG‐400	
Aldehyde		
Recyclable	
Anthranilamide	
Catalyst‐free	conditions	
2‐Phenyl‐2,3‐dihydroquinazolin‐4(1H)‐one	

	
1.	Introduction	
	

2,3‐Dihydroquinazolin‐4(1H)‐one	 derivatives	 are	 playing	
crucial	role	in	the	context	of	drug	intermediates,	biological	and	
pharmaceutical	 applications.	 Its	 analogues	 are	widely	 used	 in	
heterocyclic	 chemistry,	 medicinal	 chemistry	 [1].	 These	
derivatives	 exhibit	 good	 biological	 activities	 such	 as	 anti‐
cancer,	 antitumor,	 diuretic,	 herbicidal,	 and	 plant	 growth	
regulation	 [2].	 They	 are	 some	 marketed	 drugs	 with	
quinazolinone	 skeleton	 are	 given	 in	 Figure	 1.	 Numerous	
methods	 have	 been	 reported	 for	 the	 synthesis	 2,3‐
dihydroquinazolin‐4(1H)‐one	 derivatives	 by	 using	 different	
catalytic	 mediums	 such	 as	 KAl(SO4)2.12H2O	 [3],	 molecular	
iodine	[4],	ionic	liquids	([bmim]BF4)	[5],	montmorillonite	K‐10	
[6],	gallium(III)triflate	[7],	MCM‐41‐SO3H	[8],	silica	sulfuric	acid	
[9],	Al(H2PO4)3	[10],	and	zinc(II)perfluorooctanoate	[Zn(PFO)2]	
[11].	Wang	et	al.	developed	 the	aqueous	phase	synthesis	of	2‐
substituted‐2,3‐dihydroquinazolin‐4(1H)‐ones	 from	 anthranil‐
amide	 and	 different	 aldehydes/ketones	 [12].	 Singh	 and	 co‐
workers	 reported	 the	 synthesis	 of	 2,3‐dihydroquinazolin‐
4(1H)‐ones	 from	 isatoic	 anhydride,	 aldehyde,	 amine	 or	
ammonium	acetate	in	water	under	microwave	in	the	presence	
of	L‐proline	[13].	Arjmandi	and	co‐workers	described	the	acetic	
acid	 mediated	 synthesis	 of	 2,3‐dihydroquinazolin‐4(1H)‐ones	
from	isatoic	anhydride,	aldehyde,	amine	[14].	Recently,	Ramesh	
and	 co‐workers	 demonstrated	 the	 synthesis	 of	 2‐phenyl‐2,3‐
dihydroquinazolin‐4(1H)‐ones	 from	 anthranilamide,	 different	
aldehydes	 in	 the	 presence	 of	 β‐cyclodextrin	 water	 [15].	 The	
above	 mentioned	 methods	 suffered	 from	 one	 or	 more	
disadvantages	 such	 as	 the	 use	 of	 hazardous	 organic	 solvents,	
low	 yields,	 strongly	 acidic	 conditions,	 expensive	 moisture‐
sensitive	 catalysts,	 and	 tedious	 workup	 conditions.	 In	 past	
decades,	 polyethylene	 glycol	 (PEG‐400)	 has	 acquired	
significance	 as	 an	 eco‐friendly	 solvent	 in	 many	 organic	
reactions,	 and	 economically	 viable,	 non‐hazardous,	 and	

nontoxic	 green	 solvent.	On	 the	other	hand,	PEG	 also	 acts	 as	 a	
phase	 transfer	 catalyst	 and	 is	 used	 in	many	 synthetic	 organic	
transformations	 [16]	 such	 as	 oxidation,	 reduction	 reactions	
[17],	and	Suzuki	cross‐coupling	reaction	[18],	Wacker	reaction	
[19],	and	Heck	reaction	[20].	
	

H
N

NH

O

Cl

S
O

OH2N

N

N

O

F

H2N

N

NH

O

N

N

O

O

N
H

HO

Febrifugine

Quinazolinone

Afloqualone

Quinethazone

	
	

Figure	1.	Some	marketed	drugs	with	quinazolinone	skeleton.	
	
2.	Experimental	
	
2.1.	Instrumentation	and	material	
	

All	the	chemicals	were	purchased	from	Sigma	Aldrich	with	
purity	 not	 less	 than	 99.9%.	 Analytical	 thin	 layer	 chroma‐
tography	(TLC)	was	carried	out	by	using	silica	gel	60F254	pre‐
coated	plates.	Visualization	was	accomplished	with	UV	lamp	of	
I2	stain.	All	the	products	were	characterized	by	their	NMR	and	
Mass	 spectra.	 1H	NMR	and	 13C	NMR	were	 recorded	on	200	or	
300	MHz,	 in	 CDCl3,	 and	 the	 chemical	 shifts	 were	 reported	 in	
parts	 per	 million	 (ppm,	 δ)	 downfield	 from	 the	
tetramethylsilane.		



Yerram	et	al.	/	European	Journal	of	Chemistry	4	(4)	(2013)	462‐466	 463	
 

	

N
H

NH

O
CHO

+ NH2

O

NH2

PEG-400

100-110 oC
R

R= H, F, Br, NO2, CH3, OCH3, o-Allyloxy

R

	
	

Scheme	1.	Synthesis	of	2‐phenyl‐2,3‐dihydroquinazolin‐4(1H)‐one	derivatives.	
	
	
All	 reactions	 were	 carried	 out	 without	 any	 special	

precautions	in	an	atmosphere	of	air.	Chemicals	were	purchased	
from	Fluka	and	S.	D.	Fine	Chemicals	 and	directly	used	 for	 the	
synthesis.	 TLC:	 pre‐coated	 silica	 gel	 plates	 (60F254,	 0.2	 mm	
layer;	 E.	 Merck).	 M.p.:	 Fischer‐Johns	melting‐point	 apparatus;	
uncorrected.	 1H	 NMR	 Spectra:	 Varian	 200	 or	 Avance	 300	
spectrometer;	 in	 CDCl3;	 δ	 in	 ppm,	 J	 in	 Hz,	 Mass	 spectra:	 VG	
Autospec;	in	m/z.		
	
2.2.	Synthesis	
	

To	 a	 stirred	 solution	 of	 polyethylene	 glycol	 (5	 mL),	
anthranilamide	 (1.0	 mmol),	 and	 aldehyde	 (1.0	 mmol)	 were	
added	and	stirred	at	100‐110	oC,	for	an	appropriate	time.	After	
completion	 of	 the	 reaction,	 as	 indicated	 by	 TLC,	 the	 reaction	
mass	was	extracted	with	ethyl	acetate	(3	x	10	mL)	and	PEG	was	
separated.	 The	 combined	 organic	 layers	 were	 evaporated	
under	reduced	pressure,	and	the	crude	product	was	purified	by	
column	chromatography	by	using	hexane:EtOAc	mixture	(7:3).	
The	 recovered	 PEG	 was	 reused	 for	 three	 cycles	 without	 any	
significant	loss	of	activity	(Scheme	1).	

2‐Phenyl‐2,3‐dihydroquinazolin‐4(1H)‐one	 (Entry	1):	 Color:	
White.	Yield:	85%.	M.p.:	225‐227	oC.	FT‐IR	(KBr,	,	cm‐1):	3302	
(NH),	3184	(NH),	3061	(CH)	(NH‐CH‐NH),	2924	(C=C‐H),	1658	
(C=O)	1612	(CONH).	1H	NMR	(300	MHz,	CDCl3,	δ,	ppm):	7.95	(d,	
J	=	7.5	Hz,	1H,	Ar‐H),	7.60‐7.57	(m,	2H,	Ar‐H),	7.48‐7.45	(m,	2H,	
Ar‐H),	7.36‐7.30	(m,	1H,	Ar‐H),	7.27	(s,	1H,	Ar‐H),	6.92	(t,	J	=	6.7	
Hz,	1H,	Ar‐H),	6.65	(d,	J	=	7.5	Hz,	1H,	Ar‐H),	5.92	(s,	1H,	‐NH‐CH‐
NH),	 5.79	 (s,	 1H,	 br,	 ‐CH‐NH‐CO),	 4.38	 (s,	 1H,	 br,	 Ar‐NH‐CH‐).	
13C	NMR	(50	MHz,	CDCl3,	δ,	ppm):	164.75	 (1C,	Ar‐CO),	147.22	
(2C,	Ar‐C),	138.51	(1C,	Ar‐C),	134.02	(1C,	Ar‐C),	130.16	(1C,	Ar‐
C),	 129.12	 (1C,	 Ar‐C),	 128.72	 (2C,	 Ar‐C),	 127.39	 (1C,	 Ar‐C),	
119.67	(2C,	Ar‐C),	114.55	(1C,	Ar‐C),	69.07	(1C,	NH‐CH‐NH).	MS	
(EI,	m/z	(%)):	225	[M+,	100].	

2‐(Anthracen‐9‐yl)‐2,3‐dihydroquinazolin‐4(1H)‐one	 (Entry	
2):	 Color:	White.	 Yield:	 85%.	M.p.:	 235‐237	 oC.	 FT‐IR	 (KBr,	,	
cm‐1):	 3304	 (NH),	 3188	 (NH),	 3062	 (CH)	 (NH‐CH‐NH),	 2926	
(C=C‐H),	1657	(C=O)	1611	(CONH).	1H	NMR	(300	MHz,	CDCl3,	δ,	
ppm):	8.55	(s,	1H,	Ar‐H),	8.08‐8.02	(m,	3H,	Ar‐H),	7.52‐7.35	(m,	
6H,	Ar‐H),	7.25	(m,	2H,	Ar‐H),	6.97	(t,	J	=	6.7	Hz,	1H,	Ar‐H),	6.68	
(d,	J	=	8.3	Hz,	1H,	Ar‐H),	6.23	(s,	1H,	Ar‐H),	4.64	(s,	1H,	NH‐CH‐
Ar).	 13C	 NMR	 (50	 MHz,	 CDCl3,	 δ,	 ppm):	 162.22	 (1C,	 Ar‐CO),	
130.87	(8C,	Ar‐C),	129.26	(5C,	Ar‐C),	125.35	(5C,	Ar‐C),	114.72	
(2C,	Ar‐C),	63.88	 (1C,	NH‐CH‐NH).	MS	 (EI,	m/z	 (%)):	325	 [M+,	
100].	 Anal.	 calcd.	 for	 (C22H16N2O):	 C,	 81.46;	 H,	 4.97;	 N,	 8.64.	
Found:	C,	81.40;	H,	4.91;	N,	8.60%.	

2‐(4‐Nitrophenyl)‐2,3‐dihydroquinazolin‐4(1H)‐one	 (Entry	
3):	 Color:	 Yellow	 solid.	 Yield:	 92%.	 M.p.:	 204‐206	 oC.	 FT‐IR	
(KBr,	,	cm‐1):	3278	(NH),	3174	(NH),	3032	(CH)	(NH‐CH‐NH),	
2922	 (C=C‐H),	 1647	 (C=O),	 1608	 (CONH‐),	 1520	 (C=C),	 1461	
(C=C),	1345	(C=C).	1H	NMR	(300	MHz,	CDCl3,	δ,	ppm):	8.32	(d,	J	
=	8.3	Hz,	1H,	Ar‐H),	7.97	(m,	1H,	Ar‐H),	7.84‐7.80	(m,	2H,	Ar‐H),	
7.42‐7.36	 (m,	 1H,	 Ar‐H),	 7.28	 (s,	 1H,	 Ar‐H),	 6.99‐6.91	 (m,	 1H,	
Ar‐H),	 6.71	 (d,	 J	 =	 7.5	Hz,	 1H,	Ar‐H),6.16	 (s,	 1H,	 br,	 ‐NH‐CO‐),	
6.04	 (s,	 1H),	 4.42	 (s,	 1H,	 br,	NH‐CH‐NH).	 	 13C	 NMR	 (50	MHz,	
CDCl3,	δ,	ppm)	 :	162.97	(1C,	Ar‐CO),	147.61	(1C,	Ar‐C),	146.51	
(1C,	Ar‐C),	145.96	(1C,	Ar‐C),	132.45	(2C,	Ar‐C),	126.79	(1C,	Ar‐

C),	 126.50	 (2C,	 Ar‐C),	 122.26	 (1C,	 Ar‐C),	 116.71	 (2C,	 Ar‐C),	
113.72	 (1C,	 Ar‐C),	 64.88	 (1C,	 ‐NH‐CH‐NH‐).	 MS	 (EI,	 m/z	
(%)):270	[M+,	100].	

2‐(3‐Nitrophenyl)‐2,3‐dihydroquinazolin‐4(1H)‐one	 (Entry	
4):	 Color:	 Yellow	 solid.	 Yield:	 88%.	 M.p.:	 210‐121	 oC.	 	 FT‐IR	
(KBr,	,	cm‐1):	3293	(NH),	3190	(NH),	3072	(CH)	(NH‐CH‐NH),	
2924	 (C=C‐H),	 1654	 (C=O)	 1608	 (CONH),	 1533	 (C=C),	 1461	
(C=C),	1345	(C=C).	1H	NMR	(300	MHz,	CDCl3,	δ,	ppm):	8.46	(s,	
1H,	Ar‐H),	8.31	(d,	J	=	7.9	Hz,	1H,	Ar‐H),	7.98	(t,	J	=	7.9	Hz,	2H,	
Ar‐H),	7.67	(t,	J	=	7.9	Hz,	1H,	Ar‐H),	7.38	(t,	J	=	6.9	Hz,	1H,	Ar‐H),	
6.96	(t,	J	=	6.9	Hz	,1H,	Ar‐H),	6.71	(d,	J	=	7.9	Hz,	1H,	Ar‐H),	6.06	
(s,	 1H,	 NH‐CH‐NH),	 5.92	 (s,	 1H,	 ‐NH‐CO),	 4.43	 (s,	 1H,	NH‐CH‐
Ar).	 13C	 NMR	 (50	 MHz,	 CDCl3,	 δ,	 ppm):	 163.22	 (1C,	 Ar‐CO),	
146.99	(1C,	Ar‐C),	146.13	(1C,	Ar‐C),	142.75	(1C,	Ar‐C),	132.58	
(1C,	Ar‐C),	132.14	(1C,	Ar‐C),	128.51	(1C,	Ar‐C),	126.67	(1C,	Ar‐
C),	 122.25	 (1C,	 Ar‐C),	 120.93	 (1C,	 Ar‐C),	 116.98	 (1C,	 Ar‐C),	
114.03	 (1C,	Ar‐C),	 113.68	 (1C,	Ar‐C),	 65.09	 (1C,	 ‐NH‐CH‐NH‐).	
MS	(EI,	m/z	(%)):	270	[M+,	100].	

2‐(4‐Fluorophenyl)‐2,3‐dihydroquinazolin‐4(1H)‐one	 (Entry	
5):	 Color:	White.	 Yield:	 88%.	M.p.:	 203‐204	 oC.	 FT‐IR	 (KBr,	,	
cm‐1):	 3300	 (NH),	 3183	 (NH),	 3066	 (CH)	 (NH‐CH‐NH),	 2929	
(C=C‐H),	 1658	 (C=O),	 1610	 (CONH),	 1508	 (C=C),	 1482	 (C=C),	
1345	(C=C).	1H	NMR	(300	MHz,	CDCl3,	δ,	ppm):	7.95	(d,	1H,	J	=	
8.3	Hz,	Ar‐H),	7.63‐7.58	(m,	2H,	Ar‐H),	7.38‐7.33	(m,	1H,	Ar‐H),	
7.15	(t,	J	=	8.3	Hz	2H,	Ar‐H),	6.93	(t,	J	=	8.3	Hz,	1H,	Ar‐H),	6.67	
(d,	 J	=	8.3	Hz,	1H,	Ar‐H),	5.92	(s,	1H,	 ‐NH‐CH‐NH),	5.79	(s,	1H,	
NH‐CO),	 4.35	 (s,	 1H,	 ‐NH‐CH‐Ar).	 13C	 NMR	 (50	MHz,	 CDCl3,	 δ,	
ppm):	161.88	(1C,	Ar‐CO),	158.68	(1C,	Ar‐C),	146.94	(1C,	Ar‐C),	
132.65	(2C,	Ar‐C),	128.28	(2C,	Ar‐C),	128.19	(1C,	Ar‐C),	126.87	
(1C,	Ar‐C),	117.84	(1C,	Ar‐C),	114.53	(1C,	Ar‐C),	114.25	(1C,	Ar‐
C),	 113.76	 (1C,	 Ar‐C),	 66.38	 (1C,	 NH‐CH‐NH).	 MS	 (EI,	 m/z	
(%)):243	[M+,	100].	

2‐(4‐Bromophenyl)‐2,3‐dihydroquinazolin‐4(1H)‐one	 (Entry	
6):	 Color:	White.	 Yield:	 89%.	M.p.:	 200‐202	 oC.	 FT‐IR	 (KBr,	,	
cm‐1):	 3306	 (NH),	 3188	 (NH),	 3060	 (CH)	 (NH‐CH‐NH),	 2927	
(C=C‐H),	 1658	 (C=O)	 1607	 (CONH),	 1533	 (C=C),	 1461	 (C=C),	
1345	(C=C).	1H	NMR	(300	MHz,	CDCl3,	δ,	ppm):	7.91	(d,	1H,	J	=	
7.1	Hz,	Ar‐H),	7.53	(d,	2H,	J	=	8.0	Hz,	Ar‐H),	7.44	(d,	2H,	J	=	8.9	
Hz,	Ar‐H),	7.32	(t,	1H,	 J	=	7.1	Hz,	Ar‐H),	6.89	(t,	1H,	J	=	7.1	Hz,	
Ar‐H),	6.64	(d,	1H,	 J	=	7.1	Hz,	Ar‐H),	5.85	(s,	1H,	‐NH‐CH‐NH	),	
5.75	 (s,	 1H,	 ‐NH‐CO),	 4.32	 (s,	 1H,	 ‐NH‐CH‐NH).	 13C	 NMR	 (50	
MHz,	 CDCl3,	 δ,	 ppm):	 163.10	 (1C,	 Ar‐CO),	 146.46	 (1C,	 Ar‐C),	
139.06	(1C,	Ar‐C),	133.14	(1C,	Ar‐C),	132.23	(1C,	Ar‐C),	130.38	
(1C,	Ar‐C),	130.10	(1C,	Ar‐C),	128.32	(1C,	Ar‐C),	127.78	(1C,	Ar‐
C),	 126.39	 (1C,	 Ar‐C),	 121.07	 (1C,	 Ar‐C),	 116.52	 (1C,	 Ar‐C),	
113.73	 (1C,	 Ar‐C),	 65.61	 (1C,	 NH‐CH‐NH).	 MS	 (EI,	m/z	 (%)):	
303	[M+,	100].	

2‐(4‐Hydroxyphenyl)‐2,3‐dihydroquinazolin‐4(1H)‐one	
(Entry	 7):	 Color:	 White.	 Yield:	 85%.	 M.p.:	 278‐280	 oC.	 FT‐IR	
(KBr,	,	cm‐1):	3305	(NH),	3189	(NH),	3061	(CH)	(NH‐CH‐NH),	
2928	 (C=C‐H),	 1659	 (C=O)	 1607	 (CONH),	 1533	 (C=C),	 1461	
(C=C),	1345	(C=C).	1H	NMR	(300	MHz,	CDCl3,	δ,	ppm):	9.34	(s,	
1H,	br,	Ar‐H),	7.76	(d,	J	=	7.7	Hz,	1H,	Ar‐H),	7.38	(d,	J	=	7.1	Hz,	
3H,	Ar‐H),	7.23	(t,	J	=	7.3	Hz,	1H,	Ar‐H),	6.84‐6.68	(m,	4H,	Ar‐H),	
6.29	(s,	1H,	‐CO‐NH‐CH‐NH),	5.73	(s,	1H,	NH‐CH‐NH).	13C	NMR	
(50	MHz,	CDCl3,	δ,	ppm):	160.99	(1C,	Ar‐CO),	156.33	(1C,	Ar‐C),	
146.67	(2C,	Ar‐C),	132.72	(2C,	Ar‐C),	128.08	(3C,	Ar‐C),	118.91	



464	 Yerram	et	al.	/	European	Journal	of	Chemistry	4	(4)	(2013)	462‐466	
	
(2C,	Ar‐C),	115.66	(1C,	Ar‐C),	113.90	(1C,	Ar‐C),	65.60	(1C,	NH‐
CH‐NH).		MS	(EI,	m/z	(%)):	241	[M+,	100].	

2‐(p‐Tolyl)‐2,3‐Dihydroquinazolin‐4(1H)‐one	 (Entry	 8):	
Color:	White.	Yield:	86%.	M.p.:	223‐225	oC.	FT‐IR	(KBr,	,	cm‐1):	
3310	(NH),	3192	(NH),	3060	(CH)	(NH‐CH‐NH),	2924	(C=C‐H),	
1662	(C=O)	1607	(CONH),	1509	(C=C),	1461	(C=C),	1345	(C=C).	
1H	NMR	(300	MHz,	CDCl3,	δ,	ppm):	7.94	(d,	J	=	7.2	Hz,	1H,	Ar‐H),	
7.45	(d,	J	=	8.3	Hz,	2H,	Ar‐H),	7.35‐7.24	(m,	3H,	Ar‐H),	6.90	(t,	J	=	
7.2	Hz,	1H,	Ar‐H),6.66	(d,	J	=	7.2	Hz,	1H,	Ar‐H),	5.87	(s,	1H,	Ar‐
H),	 5.77	 (s,	 1H,	 NH‐CO),	 4.35	 (s,	 1H,	 NH‐CH),	 2.40	 (s,	 3H,	 Ar‐
CH3).	 13C	 NMR	 (50	 MHz,	 CDCl3,	 δ,	 ppm):	 167.16	 (1C,	 Ar‐CO),	
133.98	(3C,	Ar‐C),	129.74	(2C,	Ar‐C),	128.68	(2C,	Ar‐C),	127.28	
(2C,	Ar‐C),	119.62	(2C,	Ar‐C),	114.54	(1C,	Ar‐C),	68.85	(1C,	NH‐
CH‐NH),	29.56	(1C,	Ar‐CH3).	MS	(EI,	m/z	(%)):	239	[M+,	100].	

2‐(2‐Methoxyphenyl)‐2,3‐dihydroquinazolin‐4(1H)‐one	
(Entry	 9):	 Color:	 White.	 Yield:	 87%.	 M.p.:	 184‐186	 oC.	 FT‐IR	
(KBr,	,	cm‐1):	3448	(NH),	3315	(NH),	3183	(CH)	(NH‐CH‐NH),	
2923	 (C=C‐H),	 1676	 (C=O)	 1599	 (CONH),	 1473	 (C=C),	 1345	
(C=C).	1H	NMR	(300	MHz,	CDCl3,	δ,	ppm):	8.56‐8.53	(m,	1H,	Ar‐
H),	8.33‐8.29	(m,	1H,	Ar‐H),	7.81‐7.74	(m,	1H,	Ar‐H),	7.56‐7.41	
(m,	2H,	Ar‐H),	7.18	(t,	J	=	6.7	Hz,	1H,	Ar‐H),	7.07	(d,	J	=	6.7	Hz,	
1H,	 Ar‐H),	 6.91‐6.87	 (m,	 1H,	 Ar‐H),	 6.66‐6.62	 (m,	 1H,	 Ar‐H),	
6.56	(t,	J	=	6.7	Hz,	1H,	Ar‐H),	4.43	(s,	1H,	NH‐CH),	4.06	(s,	3H,	O‐
CH3).	 13C	 NMR	 (50	 MHz,	 CDCl3,	 δ,	 ppm):	 170.55	 (1C,	 Ar‐CO),	
155.93	(1C,	Ar‐C),	148.33	1C,	Ar‐C),	132.68	(1C,	Ar‐C),	131.05	
(1C,	Ar‐C),	129.24	(1C,	Ar‐C),	127.60	(1C,	Ar‐C),	126.46	(1C,	Ar‐
C),	 125.90	 (1C,	 Ar‐C),	 124.76	 (1C,	 Ar‐C),	 124.38	 (1C,	 Ar‐C),	
119.35	 (1C,	 Ar‐C),	 118.65	 (1C,	 Ar‐C),	 70.34	 (1C,	 NH‐CH‐NH‐),	
54.38	(1C,	Ar‐O‐CH3).	MS	(EI,	m/z	(%)):	255	[M+,	100].	

2‐(4‐(Allyloxy)phenyl)‐2,3‐dihydroquinazolin‐4(1H)‐one	
(Entry	10):	 Color:	White.	 Yield:	 84%.	M.p.:	 220‐222	 oC.	 FT‐IR	
(KBr,	,	cm‐1):	3299	(NH),	3187	(NH),	3061	(CH)	(NH‐CH‐NH),	
2922	 (C=C‐H),	 1651	 (C=O)	 1611	 (CONH),	 1509	 (C=C),	 1484	
(C=C).	1H	NMR	(300	MHz,	CDCl3,	δ,	ppm):	7.94	(d,	J	=	6.8	Hz,	1H,	
Ar‐H),	7.48	(d,	J	=	8.0	Hz,	2H,	Ar‐H),	7.33	(t,	J	=	8.0	H,	1H,	Ar‐H),	
6.96	(d,	J	=	8.0	Hz,	2H,	Ar‐H),	6.88	(t,	J	=	8.0	Hz,	1H,	Ar‐H),	6.66	
(d,	 J	 =	8.0	Hz,	1H,	Ar‐H),	6.08‐6.00	 (m,	 1H,	Ar‐H),	5.85	 (s,	 1H,	
NH‐CH‐NH),	5.72	(s,	1H,	NH‐CO),	5.41	(d,	J	=	17.1	Hz,	1H,	‐C=C‐
H),	 5.31	 (d,	 J	 =	 9.1	Hz,	 1H,	 C=C‐H),	 4.56	 (d,	 J	 =	 5.7	Hz,	 2H,	O‐
CH2),	 4.34	 (s,	 1H,	 NH‐CH).	 13C	NMR	 (50	MHz,	 CDCl3,	 δ,	 ppm):	
161.91	 (1C,	 Ar‐CO),	 147.35	 (1C,	 Ar‐C),	 133.97	 (1C,	 O‐CH2‐
CH=CH2),	132.86	(1C,	Ar‐C),	131.75	(1C,	Ar‐C),	129.15	(1C,	Ar‐
C),	 127.85	 (1C,	 Ar‐C),	 127.16	 (1C,	 Ar‐C),	 125.74	 (1C,	 Ar‐C),	
125.48	(1C,	Ar‐C),	119.72	(1C,	Ar‐C),	117.22	(1C,	Ar‐C),	116.87	
(1C,	 O‐CH2‐CH=CH2),	 114.13	 (1C,	 Ar‐H),	 113.90	 (1C,	 Ar‐H),	
68.04	 (1C,	 NH‐CH‐NH),	 67.87	 (1C,	 ‐O‐CH2).	 MS	 (EI,	m/z	 (%)):	
281	[M+,	100].	

2‐(2,5‐Dimethylphenyl)‐2,3‐dihydroquinazolin‐4(1H)‐one	
(Entry	11):	 Color:	White.	 Yield:	 85%.	M.p.:	 223‐225	 oC.	 FT‐IR	
(KBr,	,	cm‐1):	3312	(NH),	3192	(NH),	3061	(CH)	(NH‐CH‐NH),	
2924	(C=C‐H),	1662	(C=O)	1607	(CONH),	1509	(C=C).	1H	NMR	
(300	MHz,	CDCl3,	δ,	ppm):	7.88	(d,	J	=	6.9	Hz,	1H,	Ar‐H),	7.51	(s,	
1H,	Ar‐H),	7.31	(t,	J	=	6.9	Hz,	1H,	Ar‐H),	7.07	(s,	3H,	Ar‐H),	6.86	
(t,	 J	=	6.9	Hz,	1H,	Ar‐H),	6.68	(d,	 J	=	7.9	Hz,	1H,	Ar‐H),	6.21	(s,	
1H,	NH‐CO),	6.08	(s,	1H,	NH‐CH‐NH),	2.38	(s,	3H,	Ar‐CH3),	2.31	
(s,	3H,	Ar‐CH3).	 13C	NMR	(50	MHz,	CDCl3,	δ,	ppm):	163.18	(1C,	
Ar‐CO),	147.13	(1C,	Ar‐C),	135.71	(1C,	Ar‐C),	133.43	(1C,	Ar‐C),	
131.61	(1C,	Ar‐C),	129.06	(1C,	Ar‐C),	127.66	(1C,	Ar‐C),	126.68	
(1C,	Ar‐C),	126.01	(1C,	Ar‐C),	125.15(	1C,	Ar‐C),	124.64	(1C,	Ar‐
C),	 115.85	 (1C,	 Ar‐C),	 113.35	 (1C,	 Ar‐C),	 63.56	 (1C,	 NH‐CH‐
NH),19.25	 (1C,	Ar‐CH3),	16.85	 (1C,	Ar‐CH3).	MS	(EI,	m/z	 (%)):	
253	[M+,	100].	

2‐(3,4‐Dihydroxyphenyl)‐2,3‐dihydroquinazolin‐4(1H)‐one	
(Entry	12):	 Color:	White.	 Yield:	 84%.	M.p.:	 290‐292	 oC.	 FT‐IR	
(KBr,	,	cm‐1):	3313	(NH),	3193	(NH),	3062	(CH)	(NH‐CH‐NH),	
2925	(C=C‐H),	1663	(C=O),	1608	(CONH),	1510	(C=C).	1H	NMR	
(300	MHz,	CDCl3,	δ,	ppm):	8.84	(s,	1H,	br,	Ar‐H),	7.80‐7.57	(m,	
2H,	Ar‐H),	7.41	(t,	J	=	7.5	Hz,	1H,	Ar‐H),	7.21	(t,	J	=	7.1	Hz,	1H,	
Ar‐H),	7.04	(s,	1H,	Ar‐H),	6.89	(d,	J	=	8.3	Hz,	1H,	Ar‐H),	6.80‐6.66	
(m,	2H,	Ar‐H),	5.65	(s,	1H,	CH‐NH),3.59	(s,	2H,	Ar‐OH).	13C	NMR	

(50	MHz,	CDCl3,	δ,	ppm):	162.67	(1C,	Ar‐CO),	150.88	(1C,	Ar‐C‐
OH),	147.85	(1C,	Ar‐C‐OH),	147.44	(1C,	Ar‐C),	146.85	(1C,	Ar‐C),	
146.28	(1C,	Ar‐C),143.96	(1C,	Ar‐C),	143.65	(1C,	Ar‐C),	143.37	
(1C,	Ar‐C),	132.98	(1C,	Ar‐C),	130.58	(1C,	Ar‐C),	125.77	(1C,	Ar‐
C),	118.24	(1C,	Ar‐C),	64.98	(1C,	NH‐CH‐NH).	MS	(EI,	m/z	(%)):	
257	[M+,	100].	

2‐(1H‐Indol‐3‐yl)‐2,3‐dihydroquinazolin‐4(1H)‐one	 (Entry	
13):	Color:	White.	Yield:	80%.	M.p.:	232‐235	oC.	FT‐IR	(KBr,	,	
cm‐1):	 3311	 (NH),	 3191	 (NH),	 3060	 (CH)	 (NH‐CH‐NH),	 2923	
(C=C‐H),	1661	(C=O),	1606	(CONH),	1508	(C=C).	1H	NMR	(300	
MHz,	 CDCl3,	 δ,	 ppm):	 10.08	 (s,	 1H,	 Ar‐H),	 8.92	 (s,	 1H,	 Ar‐H),	
8.34‐8.30	(m,	3H,	Ar‐H),	7.85	(d,	J	=	3.0	Hz,	2H,	Ar‐H),	7.44	(t,	J	=	
5.1	Hz,	2H,	Ar‐H),	7.35‐7.30	(m,	2H,	Ar‐H),	5.81	(s,	1H,	CH‐NH),	
4.94	(s,	1H,	NH‐Ar).	 13C	NMR	(50	MHz,	CDCl3,	δ,	ppm):	161.43	
(1C,	 Ar‐CO),	 151.71	 (1C,	 Ar‐C),	 136.02	 (2C,	 Ar‐C),	 133.74	 (2C,	
Ar‐C),	131.83	 (1C,	Ar‐C),	131.28	 (1C,	Ar‐C),	128.14	 (2C,	Ar‐C),	
127.13	 (1C,	Ar‐C),	 126.22	 (2C,	Ar‐C),	 115.96	 (2C,	Ar‐C),	 67.74	
(1C,	NH‐CH‐NH).	MS	(EI,	m/z	(%)):	264	[M+,	100].	

2‐(Thiophen‐2‐yl)‐2,3‐dihydroquinazolin‐4(1H)‐one	 (Entry	
14):	Color:	White.	Yield:	81%.	M.p.:	211‐213	oC.	FT‐IR	(KBr,	,	
cm‐1):	 3448	 (NH),	 2923	 (NH),	 2853	 (CH)	 (NH‐CH‐NH),	 1763	
(C=O),	 1651	 (CONH),	 1457	 (C=C),	 1376	 (C=C).	 1H	 NMR	 (300	
MHz,	CDCl3,	δ,	ppm):	7.93	(d,	J	=	7.5	Hz,	1H,	Ar‐H),	7.41‐7.32	(m,	
2H,	Ar‐H),	7.22	(d,	J	=	3.7	Hz,	1H,	Ar‐H),	7.02	(t,	J	=	4.5	Hz,	1H,	
Ar‐H),	6.92	(t,	J	=	7.5	Hz,	1H,	Ar‐H),	6.70	(d,	J	=	8.3	Hz,	1H,	Ar‐H),	
6.20	 (s,	 1H,	NH‐CH‐NH),	6.13	 (s,	 1H,	NH‐CO),	4.56	 (s,	1H,	NH‐
CH).	 13C	 NMR	 (50	 MHz,	 CDCl3,	 δ,	 ppm):	 161.95	 (1C,	 Ar‐CO),	
132.33	(1C,	Ar‐C),	126.49	(1C,	Ar‐C),	125.26	(1C,	Ar‐C),	124.89	
(2C,	Ar‐C),	124.76	(1C,	Ar‐C),	116.93	(2C,	Ar‐C),	113.72	(1C,	Ar‐
C),	102.96	(1C,	Ar‐C),	62.28	(1C,	NH‐CH‐NH).	MS	(EI,	m/z	(%)):	
231	[M+,	100].	Anal.	calcd.	for	(C12H10N2OS):	C,	62.59;	H,	4.38;	N,	
12.16.	Found:	C,	62.51;	H,	4.24;	N,	12.12%.	

2‐(1H‐Pyrrol‐2‐yl)‐2,3‐dihydroquinazolin‐4(1H)‐one	 (Entry	
15):	Color:	White.	Yield:	82%.	M.p.:	160‐162	oC.	FT‐IR	(KBr,	,	
cm‐1):	 3293	 (NH),	 3190	 (NH),	 3072	 (CH)	 (NH‐CH‐NH),	 2923	
(C=C‐H),	1654	(C=O),	1608	(CONH),	1533	(C=C).	1H	NMR	(300	
MHz,	CDCl3,	δ,	ppm):	8.33‐8.23	(m,	1H,	Ar‐H),	8.12	(s,	2H,	Ar‐H),	
7.91‐7.75	(m,	1H,	Ar‐H),	7.56‐7.46	(m,	2H,	Ar‐H),	7.35	(d,	J	=	1.5	
Hz,	1H,	Ar‐H),	6.88	(t,	J	=	7.5	Hz,	1H,	Ar‐H),	6.78	(s,	1H,	NH‐CO‐
Ar),	 6.66	 (s,	 1H,	NH‐CH‐NH),	5.09	 (s,	1H,	NH‐CH‐Ar).	 13C	NMR	
(50	MHz,	CDCl3,	δ,	ppm):	160.52	(1C,	Ar‐CO),	151.88	(1C,	Ar‐C),	
147.34	(1C,	Ar‐C),	143,65	(1C,	Ar‐C),	132.91	(2C,	Ar‐C),	125.86	
(1C,	Ar‐C),	125.46	(2C,	Ar‐C),	124.78	(2C,	Ar‐C),	62.54	(1C,	NH‐
CH‐NH).	MS	(EI,	m/z	(%)):	214	[M+,	100].	

2‐(Pyridin‐4‐yl)‐2,3‐dihydroquinazolin‐4(1H)‐one	 (Entry	
16):	Color:	White.	Yield:	82%.	M.p.:	184‐186	oC.	FT‐IR	(KBr,	,	
cm‐1):	 3290	 (NH),	 3190	 (NH),	 3071	 (CH)	 (NH‐CH‐NH),	 2925	
(C=C‐H),	1652	(C=O),	1604	(CONH),	1535	(C=C),	1461	(C=C).	1H	
NMR	(300	MHz,	CDCl3,	δ,	ppm):	8.90	(d,	 J	=	6.0	Hz,	2H,	Ar‐H),	
8.37	(d,	J	=	7.5	Hz,	2H,	Ar‐H),	8.17	(d,	J	=	4.5	Hz,	2H,	Ar‐H),	7.87	
(d,	 J	 =	3.0	Hz,	2H,	Ar‐H),	7.62‐7.57	 (m,	1H,	Ar‐H),	5.80	 (s,	 1H,	
NH‐CH‐NH),	 5.01	 (s,	 1H,	 NH‐Ar).	 13C	 NMR	 (50	MHz,	 CDCl3,	 δ,	
ppm):	160.94	(1C,	Ar‐CO),	147.98	(1C,	Ar‐C),	146.87	(1C,	Ar‐C),	
132.95	(2C,	Ar‐C),	126.33	(2C,	Ar‐C),	125.84	(1C,	Ar‐C),	124.46	
(2C,	 Ar‐C),	 120.20	 (2C,	 Ar‐C),	 69.15	 (1C,	 NH‐CH‐NH).	 MS	 (EI,	
m/z	(%)):	226	[M+,	100].	

2‐Phenethyl‐2,3‐dihydroquinazolin‐4(1H)‐one	 (Entry	 17):	
Color:	White.	Yield:	79%.	M.p.:	210‐212	oC.	FT‐IR	(KBr,	,	cm‐1):	
3293	(NH),	3190	(NH),	3072	(CH)	(NH‐CH‐NH),	2922	(C=C‐H),	
1695	 (C=O),	 1603	 (CONH),	 1533	 (C=C).	 1H	 NMR	 (300	 MHz,	
CDCl3,	δ,	ppm):	7.86	(d,	J	=	8.1	Hz,	1H,	Ar‐H),	7.38‐7.22	(m,	4H,	
Ar‐H),	 6.84	 (t,	 J	 =	 7.2	 Hz,	 1H,	 Ar‐H),	 6.67‐6.53	 (m,	 3H,	 Ar‐H),	
5.76	(s,	1H,	NH‐CO),	4.90	(t,	J	=	5.4	Hz,	1H,	CH‐CH2),	4.11	(s,	1H,	
NH‐CH‐NH),	2.88‐2.74	(m,	2H,	CH2‐CH2	‐Ar),	2.13‐2.09	(q,	J	=	7.2	
Hz,	 2H,	 ‐CH‐CH2‐CH2	 ‐Ar).	 13C	 NMR	 (50	 MHz,	 CDCl3,	 δ,	 ppm):	
170.32	 (1C,	 Ar‐CO),	 147.72	 (1C,	 Ar‐C),	 140.01	 (1C,	 Ar‐C),	
132.83	(1C,	Ar‐C),	131.85	(1C,	Ar‐C),	130.74	(1C,	Ar‐C),	127.42	
(1C,	Ar‐C),	126.91	(1C,	Ar‐C),	124.41	(1C,	Ar‐C),	116.05	(1C,	Ar‐
C),	 115.77	 (1C,	 Ar‐C),	 113.78	 (1C,	 Ar‐C),	 113.22	 (1C,	 Ar‐C),	



Yerram	et	al.	/	European	Journal	of	Chemistry	4	(4)	(2013)	462‐466	 465	
 

63.01	 (1C,	NH‐CH‐NH),	35.59	 (1C,	Ar‐CH2‐CH2),	27.98	 (1C,	Ar‐
CH2‐CH2).	MS	(EI,	m/z	(%)):	253	[M+,	100].	

(E)‐2‐Styryl‐2,3‐dihydroquinazolin‐4(1H)‐one	 (Entry	 18):	
Color:	White.	Yield:	78%.	M.p.:	209‐211	oC.	FT‐IR	(KBr,	,	cm‐1):	
3296	(NH),	3191	(NH),	3071	(CH)	(NH‐CH‐NH),	2925	(C=C‐H),	
1658	(C=O),	1610	(CONH).	 1H	NMR	(300	MHz,	CDCl3,	δ,	ppm):	
7.88	(d,	J	=	8.2	Hz,	1H,	Ar‐H),	7.41‐7.31	(m,	6H,	Ar‐H),	6.87	(t,	J	=	
7.1	Hz,	1H,	Ar‐H),	6.72‐6.65	(m,	3H,	Ar‐H),	6.36‐6.32	(q,	J	=	16.4	
Hz,	1H,	NH‐CH‐NH),	5.45	(d,	J	=	8.2	Hz,	1H,	CH=CH‐Ar),	4.37	(s,	
1H,	NH‐CH).	13C	NMR	(50	MHz,	CDCl3,	δ,	ppm):	160.46	(1C,	Ar‐
CO),	 149.85	 (1C,	 Ar‐C),	 147.98	 (1C,	 Ar‐C),	 147.28	 (1C,	 Ar‐C),	
146.96	(1C,	Ar‐C),	138.92	(1C,	Ar‐C),	136.88	(1C,	Ar‐C),	132.40	
(1C,	Ar‐C),	127.20	(1C,	Ar‐C),	126.64	(1C,	Ar‐C),	125.93	(1C,	Ar‐
C),	 124.38	 (1C,	 Ar‐C),	 124.21	 (1C,	 Ar‐C),	 124.12	 (1C,	 NH‐CH‐
CH=CH‐Ar),	119.25	(1C,	NH‐CH‐CH=CH‐Ar),	63.01	(1C,	NH‐CH‐
NH).	MS	(EI,	m/z	(%)):	251	[M+,	100].	
	
3.	Results	and	discussion		

	
In	 continuation	 of	 our	 efforts	 toward	 the	 development	 of	

novel	 environmentally	 benign/eco‐friendly	 methodologies	
which	include	the	synthesis	of	heterocyclic	compounds,	herein,	
we	 report	 a	 mild	 and	 efficient	 one‐pot	 protocol	 for	 the	
synthesis	of	2‐phenyl‐2,3‐dihydroquinazolin‐4(1H)‐one	deriva‐
tives	 for	 the	 first	 time	by	a	 two‐component	reaction	 involving	
anthranilamide,	and	aldehyde	using	a	PEG‐400	as	a	recyclable	
reaction	medium	(Scheme	1).	 In	our	 initial	studies	toward	the	
development	 of	 this	methodology,	 anthranilamide	 (1.0	mmol)	
was	 reacted	 with	 aldehyde	 (1.0	 mmol)	 in	 PEG‐400	 at	 room	
temperature	 yielding	 the	 corresponding	 2‐phenyl‐2,3‐dihydro	
quinazolin‐4(1H)‐one	 in	 48%	 yield	 after	 5	 h.	When	 the	 same	
reaction	was	attempted	in	PEG‐400	at	100‐110	°C	the	reaction	
proceeded	 to	 completion	 within	 10	 h	 and	 yielded	 the	
corresponding	 2‐phenyl	 2,3‐dihydroquinazolin‐4(1H)‐one	 in	
85	 %	 yield	 (Table	 1).	 In	 all	 these	 reactions	 PEG‐400	 can	 be	
recovered	and	reused.	Several	examples	illustrating	this	simple	
and	practical	methodology	are	 summarized	 in	Table	1.	All	 the	
products	 were	 characterized	 by	 1H,	 13C	 NMR,	 IR,	 and	 mass	
spectra	and	compared	with	the	authentic	samples	[15].		
	
Table	1.	Synthesis	of	2‐phenyl‐2,3‐dihydroquinazolin‐4(1H)‐one	
derivatives.a	
Entry	 Aldehyde	 Product	 Yield	(%)	b
1	

	

	

85	

2	

	

	

85

3	

	

	

92	

4	

	
	

88

5	

	

	

88

6	

	

	

89	

7	

	

	

85

	 	 	
a	 Reaction	 conditions:	 aromatic	 aldehyde	 (1.0	 mmol),	 anthranilamide	 (1.0	
mmol),	PEG‐400	(5	mL),	100‐110	°C,	4‐10	h.	
b	Isolated	yield.	

Table	1.	(Continued). 
Entry	 Aldehyde	 Product	 Yield	(%)	b	
8

	

	

86	

9

	

	

87	

10	

	
H
N

NH

O

O

	

84	

11	

	

	

85	

12

	

	

84	

13

	

80	

14	
	

	

81	

15

	

	

82	

16	

N

CHO

	
	

82	

17	 	

	

79	

18 	

	

78	

a	 Reaction	 conditions:	 aromatic	 aldehyde	 (1.0	 mmol),	 anthranilamide	 (1.0	
mmol),	PEG‐400	(5	mL),	100‐110	°C,	4‐10	h.	
b	Isolated	yield.	
	
4.	Conclusion	

	
In	summary,	we	have	described	a	simple,	efficient,	and	eco‐

friendly	 protocol	 for	 the	 synthesis	 of	 2‐phenyl‐2,3‐dihydro	
quinazolin‐4(1H)‐one	 derivatives	 in	 excellent	 yields	 under	
neutral	conditions	in	one‐pot	catalyzed	by	recyclable	PEG‐400.		
	
Acknowledgement	
	

The	 authors	 are	 thankful	 to	 Malkapuram	 Srinivasa	 Rao,	
Head,	 Department	 of	 Chemistry,	 Kakatiya	 University,	 and	
Warangal	 for	the	facilities	and	to	the	Director,	Indian	Institute	
of	 Chemical	 Technology,	 Hyderabad	 for	 recording	 1H	 and	 13C	
NMR	and	mass	spectra.		
	
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